Pesticidal compounds

ABSTRACT

A compound of formula (I) wherein R1 to R4 are, for example, each hydrogen, R5 is, for example, a substituted phenol; R6 is, for example, hydrogen; R7 is, for example, hydrogen, cyano, hydroxyl, formyl, C1-C4-alkyl, C1-C4-alkoxy, C2-C4-alkenyl, or C2-C4-alkynyl; and A1 to A5 is, for example, A1 is N or C—X, A3 is C—X, and A2, A4 and A5 are C—H, where X, is, for example, halogen; and its use as a pesticidal agent.

This application is a 371 filing of International Application No.PCT/EP2012/071525, filed Oct. 31, 2012, which claims priority benefit toEP Patent No. 11187914.4 filed Nov. 4, 2011 and EP Patent No. 12179208.9filed Aug. 3, 2012, the contents of all of which are incorporated hereinby reference.

The present invention relates to certainN-[1-(2-phenyl)cyclopropylmethyl]heteroaryl carboxamide derivatives, toprocesses for their preparation, to compositions comprising thosecompounds, and to their use in agriculture and veterinary fields. andfields relying on pest management. The compounds are especially activefor controlling damage to plants by pests and fungal diseases inagriculture.

Inventors have found that certainN-[1-(2-phenyl)cyclopropylmethyl]heteroaryl carboxamide derivatives areespecially active for controlling damage by pests & fungal diseases, inparticular nematode pests.

Accordingly, the present invention relates to a compound of formula (I)compound of the formula (I) wherein

whereinR1 is hydrogen, methyl or a halogen;R2 is hydrogen, methyl or a halogen;R3 is hydrogen, methyl or a halogen;R4 is hydrogen, methyl or a halogen;R5 is substituted or unsubstituted phenyl group;R6 is hydrogen or C1-C4-alkyl;R7 is hydrogen, cyano, hydroxyl, formyl, C1-C4-alkyl, C1-C4-alkoxy,C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkoxy-C1-C4-alkyl,C1-C4-cyanoalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, benzyl,C3-C6-cycloalkylcarbonyl or C3-C6-cycloalkoxycarbonyl;A1 is N, C—H or C—X;A2 is N, C—H or C—X;A3 is N, C—H or C—X;A4 is N, C—H or C—X;A5 is N, C—H or C—X;provided wherein A1 & A5 are each N, then A2 to A4 are independentlyselected from CH, CX and N; or wherein A2 is CX, then A1, A3 to A5 areindependently selected from CH, N or CX; or wherein A1 is CX and A5 isN, then A2 to A4 are independently selected from CX and CH; or whereinA1 is CX and A5 is CH, then one of A2 to A4 is CX and the remaining areeach CH; or wherein A1 is CX and A4 is N, then A2, A3 and A5 areindependently selected from CX and CH;X is a halogen, OH, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy orC1-C4-haloalkoxy;with the proviso that at most three of A1 to A5 are N;as well as its acceptable salts, enantiomers, diastereomers, tautomers,and N-oxides.

The compounds of formula (I) and, where appropriate, the tautomersthereof, in each case in free form or in salt form, can be present inthe form of one of the isomers which are possible or as a mixture ofthese, for example in the form of pure isomers, such as antipodes and/ordiastereomers, or as isomer mixtures, such as enantiomer mixtures, forexample racemates, diastereomer mixtures or racemate mixtures, dependingon the number, absolute and relative configuration of asymmetric carbonatoms which occur in the molecule and/or depending on the configurationof non-aromatic double bonds which occur in the molecule; the inventionrelates to the pure isomers and also to all isomer mixtures which arepossible and is to be understood in each case in this sense hereinaboveand hereinbelow, even when stereochemical details are not mentionedspecifically in each case. This invention accordingly covers all suchisomers and tautomers and mixtures thereof in all proportions as well asisotopic forms such as deuterated compounds. As an example, thecompounds of the invention may contain one or more asymmetric carbonatoms, for example, at the —CR⁶—, —CR⁵—, —CR¹R²—, and —CR³R⁴— groups,and the compounds of formula (I) may exist as enantiomers (or as pairsof diastereoisomers) or as mixtures of such.

The invention also covers salts and N-oxides of each compound forformula (I).

One skilled in the art also recognizes that because in the environmentand under physiological conditions salts of chemical compounds are inequilibrium with their corresponding non salt forms, salts share thebiological utility of the non salt forms.

Thus a wide variety of salts of compounds of the invention (and activeingredients used in combination with the active ingredients of theinvention) may be useful for control of invertebrate pests and animalparasites. Salts amongst agriculturally and/or physiologically tolerablesalts include acid-addition salts with inorganic or organic acids suchas hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic,butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic,tartaric, 4-toluenesulfonic or valeric acids.

Suitable amongst agriculturally and/or physiologically tolerable saltscan also be the salts of those cations which do not adversely affect thepesticidal and/or parasiticidal action of the compounds of formula (I).Thus, especially suitable cations are the ions of the alkali metalsincluding sodium, potassium and lithium, of the alkaline earth metalsincluding calcium and magnesium, and of the transition metals includingmanganese, copper, iron, zinc, cobalt, lead, silver, nickel, and alsoammonium or organic ammonium including monoalkylammonium,dialkylammonium, trialkylammonium, tetraalkylammonium,monoalkenylammonium, dialkenylamonium, trialkenylamonium,monoalkynylammonium, dialkynylamonium, monoalkanolammonium,dialkanolammonium, C5-C6-cycloalkylammonium, piperidinium, morpholinium,pyrrolidinium, or benzylammonium, moreover phosphonium ions, sulfoniumions, preferably tri(C1-C4-alkyl) sulfonium and sulfoxonium ions,preferably tri (C1-C4-alkyl) sulfoxonium.

Alkyl groups (either alone or as part of a larger group, such asalkoxy-, alkylsulfanyl-, alkylsulfinyl-, alkylsulfonyl-, alkylcarbonyl-or alkoxycarbonyl-) can be in the form of a straight or branched chainand are, for example, methyl, ethyl, propyl, prop-2-yl, butyl, but-2-yl,or 2-methyl-prop-2-yl. The alkyl group (either alone or as part of alarger group, such as alkoxy-, alkylsulfanyl-, alkylsulfinyl-,alkylsulfonyl-, alkylcarbonyl- or alkoxycarbonyl-), in each embodimentof the invention, is preferably C1-C3-alkyl, more preferablyC1-C2-alkyl, especially methyl group. In the instance of alkoxy,examples are methoxy, ethoxy, propoxy, n-butoxy, isobutoxy and alsotheir isomeric groups; preferably, independent of other embodiments,methoxy and ethoxy, especially methoxy.

Alkenyl groups can be in the form of straight or branched chains, andcan be, where appropriate, of either the (E)- or (Z)-configuration.Examples are vinyl and allyl. The alkenyl group, in each embodiment ofthe invention, is preferably a C2-C3-alkenyl group, more preferablyvinyl or allyl group.

Alkynyl groups can be in the form of straight or branched chains.Examples are ethynyl and propargyl. The alkynyl group, in eachembodiment of the invention, is preferably a C2-C3-alkynyl group, morepreferably propargyl group.

Halogen is fluorine, chlorine, bromine or iodine; halogen, in eachembodiment of the invention, is fluorine, chlorine, or bromine;especially fluorine or chlorine.

Haloalkyl groups (either alone or as part of a larger group, such ashaloalkoxy-, haloalkylsulfanyl-, haloalkylsulfinyl- orhaloalkylsulfonyl-) are alkyl groups which are substituted by one ormore of the same or different halogen atoms and are, for example,fluoromethyl, difluoromethyl, trifluoromethyl, chlorodifluoromethyl and2,2,2-trifluoro-ethyl. The haloalkyl group (either alone or as part of alarger group, such as haloalkoxy-, haloalkylsulfanyl-,haloalkylsulfinyl- or haloalkylsulfonyl-), in each embodiment of theinvention, haloakyl is preferably trifluoromethyl. In instance ofhaloalkoxy, examples are fluoromethoxy, difluoromethoxy,trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy,2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy and2,2,2-trichloroethoxy; preferably difluoromethoxy,2,2,2-trifluoroethoxy, 2-chloroethoxy and trifluoromethoxy

Cycloalkyl groups are mono-cyclic and are, for example, cyclopropyl,cyclobutyl, cyclopentyl and cyclohexyl. The C3-C6-cycloalkyl group, ineach embodiment of the invention, is preferably a C3-C5-cycloakyl, morepreferably a C3-C4-cycloalkyl group, especially a C3-cycloalkyl group.Where a cycloalkyl moiety is said to be substituted, the cycloalkylmoiety is preferably substituted by one to four substituents, mostpreferably by one to three substituents, such as one or twosubstituents, especially one substitutent.

Alkoxycarbonyl is, for example, methoxycarbonyl, ethoxycarbonyl,propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl,isobutoxycarbonyl, secbutoxycarbonyl and tert-butoxycarbonyl; preferredare methoxycarbonyl, ethoxycarbonyl and isopropoxycarbonyl.

Alkylsulfanyl group is, for example, methylsulfanyl, ethylsulfanyl,propylsulfanyl, isopropylsulfanyl, n-butylsulfanyl, isobutylsulfanyl,sec-butylsulfanyl and tert-butylsulfanyl Examples of haloalkylsulfanylare chloro- and/or fluoro-halogenated substituents thereof, such asdifluoromethylsulfanyl, trifluoromethylsulfanyl,chlorodifluoromethylsulfanyl and 2,2,2-trifluoro-ethylsulfanyl.

Alkylsulfinyl is, for example, methylsulfinyl, ethylsulfinyl,propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl,sec-butylsulfinyl, and tert-butylsulfinyl. Examples of haloakylsulfinylare chloro- and/or fluoro-halogenated substituents thereof, such asdifluoromethylsulfinyl, trifluoromethylsulfinyl,chlorodifluoromethylsulfinyl and 2,2,2-trifluoro-ethylsufhinyl.

Alkylsulfonyl group is, for example, methylsulfonyl, ethylsulfonyl,propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl,sec-butylsulfonyl and tert-butylsulfonyl. Examples of haloakylsulfonylare chloro- and/or fluoro-halogenated substituents thereof, such asdifluoromethylsulfonyl, trifluoromethylsulfonyl,chlorodifluoromethylsulfonyl and 2,2,2-trifluoro-ethylsulfonyl.

Alkoxyalkyl is, for example, methoxymethyl, 2-methoxyethyl,ethoxymethyl, 2-ethoxyethyl, n-propoxymethyl, 2-n-propoxyethyl,isopropoxymethyl and 1-isopropoxyethyl. The alkoxyalkyl group, in eachembodiment of the invention, is preferably a C1-C4-alkoxy-C1-C4-alkyl,more preferably a C1-C2-alkoxy-methyl, such as methoxymethyl andethoxymethyl groups.

Aryl groups (either alone or as part of a larger group, such asaryl-alkylene-) are aromatic ring systems which can be mono-, bi- ortricyclic. Examples of such rings include phenyl, naphthyl, anthracenyl,indenyl or phenanthrenyl. Preferred aryl groups are phenyl and naphthyl,phenyl being most preferred.

Examples of cycloalkylcarbonyl are cyclopropylcarbonyl,cyclobutylcarbonyl, cyclopentylcarbonyl and cyclohexylcarbonyl;preferred are cyclopropylcarbonyl and cyclobutylcarbonyl.

Examples of cycloalkoxycarbonyl are cyclopropyloxycarbonyl,cyclobutyloxycarbonyl, cyclopentyloxycarbonyl and cyclohexyloxycarbonyl;preferred are cyclopropyloxycarbonyl and cyclobutyloxycarbonyl,

In an embodiment, independent of other embodiments, at least two of R1,R2, R3 and R4 for the compound of formula (I) are hydrogens; preferablyat least three; especially each of R1, R2, R3 and R4 is hydrogen.

In an embodiment, independent of other embodiments, at least one,preferably one, of R1, R2, R3 and R4 for the compound of formula (I) ishalogen or methyl.

In an embodiment, independent of other embodiments, R5 is unsubstitutedphenyl.

In an embodiment, independent of other embodiments, R5 is substitutedphenyl having 1-5 substituents.

In an embodiment, independent of other embodiments, R5 is substitutedphenyl having 1-3 substituents.

In an embodiment, independent of other embodiments, R5 is substitutedphenyl having 2 substitutents.

In an embodiment, independent of other embodiments, R5 is substitutedphenyl having 1 substituent.

In an embodiment, independent of other embodiments, if R5 is asubstituted phenyl, the substituent(s) is, independently selected, fromhalogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy,C1-C4-haloalkoxy, C1-C4-alkylsulfanyl, C1-C4-haloalkylsulfanyl,C1-C4-alkylsulfinyl, C1-C4-haloalkylsulfinyl, C1-C4-alkylsulfonyl,C1-C4-haloalkylsulfonyl, C3-C6-cycloalkyl, which cycloalkyl isunsubstituted or substituted by one or more substituents Rx, where Rxis, independently of each other, is selected from halogen, C1-C4-alkyl,and C1-C4-haloalkyl.

In an embodiment, independent of other embodiments, if R5 is asubstituted phenyl, the substituent(s) is, independently selected, fromhalogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy, andC3-C6-cycloalkyl, which cycloalkyl is unsubstituted or substituted byone or more substituents Rx, where Rx is, independently of each other,is selected from halogen, C1-C4-alkyl, and C1-C4-haloalkyl; preferablythe substituent(s) is, independently selected, from cyano, halogen, andC1-C4-haloalkyl.

In an embodiment R5 is a cyano substituted phenyl (which is optionallyfurther substituted by halogen or trifluoromethyl),2-fluoro-4-trifluoromethyl phenyl, 2,6-difluoro-4-chloro-phenyl,2,4-difluorophenyl, 2,4,6-trifluoro phenyl, 2-fluoro-4-chloro phenyl,2-fluoro-4-bromo phenyl, 2-chloro-4-fluoro phenyl,2-chloro-4-trifluoromethyl phenyl, 3,4,5-trifluoro phenyl,2,4-dichloro-6-fluoro phenyl, 2,4-dibromo phenyl or 2,4 dichlorophenyl,wherein in each case phenyl stands for phen-1-yl.

In an embodiment, independent of other embodiments, R5 is any one of theR5 substituents depicted in Table P below.

In an embodiment, independent of other embodiments, R6 is hydrogen orC1-C2-alkyl, preferably hydrogen or methyl.

In an embodiment, independent of other embodiments, R7 is selected fromhydrogen, cyano, hydroxyl, formyl, C1-C4-alkyl, C1-C4-alkoxy,C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkoxy-C1-C4-alkyl,C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl and benzyl. Preferably R7 ishydrogen, hydroxyl, C1-C2-alkyl, C1-C2-alkoxy, C2-alkenyl, C3-alkynyl,C1-C2-alkoxy-C1-alkyl, C1-C2-alkylcarbonyl, and C1-C2-alkoxycarbonyl,especially hydrogen, hydroxyl, methyl, cyano, formyl, methoxy, allyl,propargyl, methoxycarbonyl, methoxymethyl and benzyl; especially R7 ishydrogen.

In a preferred group of compounds of formula (I), R1 to R4 are eachhydrogen; R5 is a substituted or unsubstituted phenyl; R6 is hydrogen orC1-C4-alkyl; R7 is hydrogen, C1-C4-alkylcarbonyl, orC1-C4-alkoxycarbonyl; and A1 & A5 are each N, then A2 to A4 areindependently selected from CH, CX and N; or A2 is CX, then A1, A3 to A5are independently selected from CH, N or CX; or A1 is CX and A5 is N,then A2 to A4 are independently selected from CX and CH; or A1 is CX andA5 is CH, then one of A2 to A4 is CX and the remaining are each CH; orA1 is CX and A4 is N, then A2, A3 and A5 are independently selected fromCX and CH; wherein X, independent of each other, is a halogen,C1-C4-alkyl, or C1-C4-haloalkyl.

In a further preferred group of compounds of formula (I), R1 to R4 areeach hydrogen; R5 is a di or tri-substituted phenyl, wherein thesubstituents are independently selected from halogen, cyano,C1-C4-haloalkyl, C1-C4-haloalkoxy, and C3-C6-cycloalkyl, whichcycloalkyl is unsubstituted or substituted by one or more substituentsRx, where Rx is, independently of each other, is selected from halogen,C1-C4-alkyl, and C1-C4-haloalkyl; R6 is hydrogen or C1-C4-alkyl; R7 ishydrogen, C1-C4-alkylcarbonyl, or C1-C4 alkoxycarbonyl; and A1 & A5 areeach N, then A2 to A4 are independently selected from CH, CX and N; orA2 is CX, then A1, A3 to A5 are independently selected from CH, N or CX;or A1 is CX and A5 is N, then A2 to A4 are independently selected fromCX and CH; or A1 is CX and A5 is CH, then one of A2 to A4 is CX and theremaining are each CH; or A1 is CX and A4 is N, then A2, A3 and A5 areindependently selected from CX and CH; wherein X, independent of eachother, is a halogen, C1-C4-alkyl, or C1-C4-haloalkyl; with the provisothat at most three of A1 to A5 are N; as well as its acceptable salts,enantiomers, diastereomers, tautomers, and N-oxides.

In another preferred group of compounds of formula (I), R1 to R4 areeach hydrogen; R5 is a substituted or unsubstituted phenyl; R6 ishydrogen or C1-C4-alkyl; R7 is hydrogen, C1-C4-alkylcarbonyl, orC1-C4-alkoxycarbonyl; A1 is other than C-halogen, A2 is N, and A3, A4and A5 are independently selected from CX and CH; wherein X, independentof each other, is a halogen, C1-C4-alkyl, or C1-C4-haloalkyl, as well asits acceptable salts, enantiomers, diastereomers, tautomers, andN-oxides. Preferably, in this group of compounds, A1 isC—C1-C4-haloalkyl, A2 is N, and A3, A4 and A5 are independently selectedfrom CX and CH; wherein X, independent of each other, is a halogen,C1-C4-alkyl or C1-C4-haloalkyl; preferably A1 is C—CF3, A2 is N, and A3,A4 and A5 are each CH.

In an embodiment, independent of other embodiments, X, independent ofeach other, is a halogen, C1-C4-alkyl, or C1-C4-haloalkyl, preferablyselected from bromine, chlorine, fluorine, trifluoromethyl anddifluoromethyl; especially selected from chlorine, fluorine, methyl andtrifluoromethyl.

In another preferred group of compounds of formula (I), R1 to R4 areeach hydrogen; R5 is selected from cyano substituted phenyl (which isoptionally further substituted by halogen or trifluoromethyl),2-fluoro-4-trifluoromethyl phenyl, 2,6-difluoro-4-chloro-phenyl,2,4-difluorophenyl, 2,4,6-trifluoro phenyl, 2-fluoro-4-chloro phenyl,2-fluoro-4-bromo phenyl, 2-chloro-4-fluoro phenyl,2-chloro-4-trifluoromethyl phenyl, 3,4,5-trifluoro phenyl,2,4-dichloro-6-fluoro phenyl, and 2,4-dibromo phenyl; R6 is hydrogen orC1-C4-alkyl; R7 is hydrogen, C1-C4-alkylcarbonyl, orC1-C4-alkoxycarbonyl; and A1 is C—X, and A2 to A5 are each CH; or A1 andA5 are each C—X, and A2 to A4 are each CH; or A1 is C—X, A2 and A5 areeach N, and A3 and A4 are each CH; or A1 is C—X, A2 is N, and A3 to A5are each CH, wherein X is independently selected from halogen,C—C4-alkyl or C-1-C4-haloalkyl, as well as its acceptable salts,enantiomers, diastereomers, tautomers, and N-oxides. Preferably X is,independently of the A1 to A5 configuration and independently of Xwithin a A1 to A5 configuration, selected from chlorine, fluorine,trifluoromethyl and difluoromethyl; In a preferred embodiment, A1 isC—CF3, and A2 to A5 are each CH; or A1 and A5 are each C—F, and A2 to A4are each CH; or A1 is C—CF3 or C1, A2 and A5 are each N, and A3 and A4are each CH; or A1 is C—CF3, A2 is N, and A3 to A5 are each CH.

In another preferred group of compounds of formula (I), R1 to R4 areeach hydrogen; R5 is 2,4-chloro phenyl; R6 is hydrogen or C1-C4-alkyl;R7 is hydrogen, C1-C4-alkylcarbonyl, or C1-C4-alkoxycarbonyl; and A1 isC—Cl, and A2 to A5 are each CH; or A1 is C—F, A2 and A5 are each N, andA3 and A4 are each CH; or A1 and A5 are each C—Cl or C—CF3 and A2 to A4are each CH; or A1 is C—F or C—CF3, A2 is N, and A3 to A5 are each CH;or A1 & A5 are each N, then A2 to A4 are independently selected from CH,CX and N; or A2 is CX, then A1, A3 to A5 are independently selected fromCH, N or CX; or A1 is CX and A5 is N, then A2 to A4 are independentlyselected from CX and CH; or A1 is CX and A5 is CH, then one of A2 to A4is CX and the remaining are each CH; or A1 is CX and A4 is N, then A2,A3 and A5 are independently selected from CX and CH; wherein X,independent of each other, is a halogen, C1-C4-alkyl, orC1-C4-haloalkyl, as well as its acceptable salts, enantiomers,diastereomers, tautomers, and N-oxides.

In an embodiment, independent of other embodiments, R5 is a substitutedphenyl having substituents independently selected from halogen, cyano,C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy,C3-C6-cycloalkyl, which cycloalkyl is unsubstituted or substituted byone or more substituents Rx, where Rx is, independently of each other,is selected from halogen, C1-C4-alkyl, and C1-C4-haloalkyl. Preferably,the substituents on the phenyl at R5 are independently selected fromhalogen, cyano, C1-C2-alkyl, C1-C2-haloalkyl, C1-C2-alkoxy,C1-C2-haloalkoxy, and optionally substituted C3-C4-cycloalkyl, whereinthe substituents can be independently selected from chlorine, fluorine,and trifluoromethyl.

In an embodiment, independent of other embodiments, R5 is a substitutedphenyl having one to three substituents, preferably two or threesubstituents, more preferably two substituents.

In an embodiment, independent of other embodiments, the phenyl at R5 issubstituted by an optionally substituted phenyl or optionallysubstituted pyrazole. Preferably, the substituent(s) on the phenyl orpyrazole substituted phenyl at R5 is independently selected fromchlorine, methyl, fluorine, trifluoromethyl, cyclopropyl, and cyano.

In an embodiment, independent of other embodiments, R6 is hydrogen orC1-C2-alkyl, preferably hydrogen.

In an embodiment, independent of other embodiments, R7 is hydrogen.

In an embodiment, independent of other embodiments, wherein A1 is N orC—X, and the groups A2, A3, A4 and A5 are selected from (I) A2, A3 andA4 are each C—H, and A5 is N; (II) A2 is C—X, and A3, A4 and A5 are eachC—H; (III) A3 is C—X, and A2, A4 and A5 are each C—H; (IV) A4 is C—X,and A2, A3 and A5 are each C—H; and (V) A2, A3 and A5 are each CH and A4is N.

In an embodiment, independent of other embodiments, wherein A1 & A5 areeach N, then A2 to A4 are independently selected from CH, CX and N.

In an embodiment, independent of other embodiments, wherein A2 is CX,then A1, A3 to A5 are independently selected from CH, N or CX.

In an embodiment, independent of other embodiments, wherein A1 is CX andA5 is N, then A2 to A4 are independently selected from CX and CH.

In an embodiment, independent of other embodiments, A1 is N or C—X, andA2, A3 and A4 are C—H, and A5 is N. Preferably, in this embodiment, A1is CX, A2, A3 and A4 are C—H, and A5 is N and A1 is N, A2, A3 and A4 areC—H, and A5 is N.

In an embodiment, independent of other embodiments, A1 is N or C—X, A2is C—X, and A3, A4 and A5 are each C—H.

In an embodiment, independent of other embodiments, A1 is N or C—X, A3is C—X, and A2, A4 and A5 are C—H; and

In an embodiment, independent of other embodiments, A1 is N or C—X, A4is C—X, and A2, A3 and A5 are each C—H.

In an embodiment, independent of other embodiments, A1 and A5 are N; andremaining are independently selected from C—H and C—X.

In an embodiment, independent of other embodiments, A1 is CX, A2, A3 andA5 are each CH, and A4 is CX.

In an embodiment, independent of other embodiments, A1 is CX, A2, A3 andA5 are each CH, and A4 is N.

In an embodiment, independent of other embodiments, A1 is CX, A2, A4 andA5 are each CH, and A3 is CX.

In an embodiment, independent of other embodiments, A1 is CX, A2 and A3are each CH, A4 is N and A5 is CX.

In an embodiment, independent of other embodiments, in the instance anyone of A1 to A5 is CX, X in CX is, independently selected, from halogen,C1-C4-alkyl and C1-C4-haloalkyl. Preferably X is halogen, C1-C2-alkyland C1-C2-haloalkyl, especially halogen, methyl and halomethyl, such astrifluoromethyl.

In an embodiment, independent of other embodiments, A1 isC—C1-C4-haloalkyl, A2 is N and A3, A4 and A5 are each C—H.

In an embodiment, independent of other embodiments, A1 is C—X, A2, A3and A4 are C—H, and A5 is N.

In an embodiment, independent of other embodiments, R6 is hydrogen orC1-C2-alkyl, preferably hydrogen.

In an embodiment, independent of other embodiments, R7 is hydrogen.

In an embodiment, independent of other embodiments, X in CX of the A1 toA5 is, independently selected, from halogen, C1-C2-alkyl andC1-C2-haloalkyl; preferably selected independently from chlorine,fluorine, methyl, and trifluoromethyl,

In an aspect, a compound of formula (I) is wherein R1 to R4 are eachhydrogen; R5 is a substituted or unsubstituted phenyl; R6 is hydrogen orC1-C4-alkyl; R7 is hydrogen, C1-C4-alkylcarbonyl, orC1-C4-alkoxycarbonyl; and A1 is CX, A2 and A4 are each N, and A3 & A5are each CH or A1 is CX, A3 and A5 are each N, and A2 & A4 are each CH;wherein X, independent of each other, is a halogen, C1-C4-alkyl, orC1-C4-haloalkyl.

In a preferred embodiment of each embodiment described herein, R5 is aphenyl substituted by 2 to 3 substituents independently selected fromhalogen, cyano, C1-C4-haloalkyl, C1-C4-haloalkoxy, and optionallysubstituted C3-C6-cycloalkyl; preferably independently selected fromchlorine, methyl, fluorine, trifluoromethyl, cyclopropyl, and cyano.

In a preferred embodiment of each embodiment described herein, A1 is CX,A2 and A5 is independently selected from N and CH, and A3 & A4 are eachCH wherein X is Cl, F or CF3, preferably CF3, Cl, more preferably CF3.

In an especially preferred embodiment, independent of each embodiment,A1 is CX, A2 is N and A3 to A5 are each CH wherein X is Cl, or CF3,preferably CF3, Cl, more preferably CF3; or A1 is CX, A5 is N and A2 toA4 are each CH wherein X is Cl, F or CF3, preferably CF3, Cl, morepreferably CF3; or A1 is CX, A2 & A5 are each N and A3 and A4 are eachCH wherein X is Cl, F or CF3, preferably CF3, Cl, more preferably CF3.

A preferred ring, independent of each embodiment, of A1 to A5 is A1 isC—CF3, and A2 to A5 are each CH; or A1 is C—CF3, A2 and A5 are each N,and A3 and A4 are each CH; or A1 is C-chlorine, A2 and A5 are each N,and A3 and A4 are each CH; or A1 and A5 are each is C-fluorine and A2 toA4 are each CH.

Compounds of formula (I) can be prepared from amines of the formula (II)and acylating agents of the formula (VII), wherein R1, R2, R3, R4, R5,R6, R7, A1, A2, A3, A4, and A5 are as defined herein and Xb is a leavinggroup. Typical leaving groups are halide, preferably chloride, andhydroxyl. When Xb is hydroxyl, (VII) is a carboxylic acid, and thereaction is preferably facilitated by an activating agent. Typicalactivating agents are DCC, EDCl, BOP, HBTU, BOP-Cl, PyBOP as describedin L. A. Paquette, Encyclopedia of Reagents for Organic Synthesis, Vol3. Wiley, England, 1995 pp 1751-1754. Acylating agents of the formula(VII) are known or are easily prepared by those skilled in the art.

Amines of the formula (IIa), in which R6 and R7 are H and R1, R2, R3,R4, and R5 are as defined herein, can be prepared by treating nitrilesof the formula (III) with a reducing agent. A typical reducing agent ishydrogen. Typically such a hydrogenation would be facilitated by acatalyst. Typical catalysts are metals, metal salts, or metal complexes.Other typical reducing agents are hydrides. Typical hydrides areborohydrides, or aluminium hydrides, examples of which are sodiumborohydride, diisobutylaluminium hydride, or lithium aluminium hydride.Such hydride reductions can be facilitated by the use of othercomponents such as metal salts.

Compounds of the formula (IIb) in which R7 is H and R1, R2, R3, R4, R5,and R6 are as defined herein can be prepared by treating imines of theformula (IV) with an organometallic reagent of the formula R6-Xcfollowed by hydrolysis, for example with acid, such as hydrochloricacid. Xd is an activating group, typically an acyl, sulfinyl or sulfonylgroup. Xc is a metal ion, which may or may not be coordinated with afurther anion or ligand. Typical R6Xc reagents are Grignard ororganolithium reagents.

Compounds (IVa) in which Xd is S(═O)Xf and R1, R2, R3, R4, and R5 are asdefined herein can be prepared from the aldehyde (VI) and a sulfinamideof the formula (IX), in which Xf is alkyl or aryl. This condensation isconveniently done in the presence of a dehydrating agent. Typicaldehydrating agents are titanium chloride, titanium alkoxides, magnesiumsulphate, or calcium chloride. Aldehydes of the formula (VI) can beprepared by reduction of the corresponding nitriles (III) or esters, orby oxidation of the corresponding alcohols, for example, SWERNoxidation. One of the reducing agents which can be used for reducingnitriles or esters to aldehydes is diisobutylaluminium hydride (DIBAL).

Nitriles of the formula (III), in which R1, R2, R3, R4, and R5 are asdefined herein, can be prepared from nitriles of the formula (XI), inwhich R5 is as defined herein and an alkylating agent of the formula (X)in presence of a base, in which R1, R2, R3, and R4 are as defined hereinand Xg is a leaving group. Typical leaving groups are halide andsulfonate.

It is clear that compounds of the formula (I) can be transformed toother compounds of the formula (I) through synthetic modification of thegroups R1, R2, R3, R4, R5, R6, R7, A1, A2, A3, A4, and A5. Similarlysuch transformations can be performed on the intermediates (II)-(XI).

These reactions can be conveniently performed in a solvent.

These reactions can be conveniently performed at various temperatures.

These reactions can be conveniently performed in an inert atmosphere.

Alkylation of amine is well known for deriving compounds of formula(II).

The reactants can be reacted in the presence of a base. Examples ofsuitable bases are alkali metal or alkaline earth metal hydroxides,alkali metal or alkaline earth metal hydrides, alkali metal or alkalineearth metal amides, alkali metal or alkaline earth metal alkoxides,alkali metal or alkaline earth metal acetates, alkali metal or alkalineearth metal carbonates, alkali metal or alkaline earth metaldialkylamides or alkali metal or alkaline earth metal alkylsilylamides,alkylamines, alkylenediamines, free or N-alkylated saturated orunsaturated cycloalkylamines, basic heterocycles, ammonium hydroxidesand carbocyclic amines. Examples which may be mentioned are sodiumhydroxide, sodium hydride, sodium amide, sodium methoxide, sodiumacetate, sodium carbonate, potassium tert-butoxide, potassium hydroxide,potassium carbonate, potassium hydride, lithium diisopropylamide,potassium bis(trimethylsilyl)amide, calcium hydride, triethylamine,diisopropylethylamine, triethylenediamine, cyclohexylamine,N-cyclohexyl-N,N-dimethylamine, N,N-diethylaniline, pyridine,4-(N,N-dimethylamino)pyridine, quinuclidine, N-methylmorpholine,benzyltrimethylammonium hydroxide and 1,8-diazabicyclo[5.4.0]undec-7-ene(DBU).

The reactants can be reacted with each other as such, i.e. withoutadding a solvent or diluent. In most cases, however, it is advantageousto add an inert solvent or diluent or a mixture of these. If thereaction is carried out in the presence of a base, bases which areemployed in excess, such as triethylamine, pyridine, N-methylmorpholineor N,N-diethylaniline, may also act as solvents or diluents.

The reaction is advantageously carried out in a temperature range fromapproximately −80° C. to approximately +140° C., preferably fromapproximately −30° C. to approximately +100° C., in many cases in therange between ambient temperature and approximately +80° C.

A compound of formula (I) can be converted in a manner known per se intoanother compound of formula (I) by replacing one or more substituents ofthe starting compound of formula (I) in the customary manner by(an)other substituent(s) according to the invention.

Depending on the choice of the reaction conditions and startingmaterials which are suitable in each case, it is possible, for example,in one reaction step only to replace one substituent by anothersubstituent according to the invention, or a plurality of substituentscan be replaced by other substituents according to the invention in thesame reaction step.

Salts of compounds of formula (I) can be prepared in a manner known perse. Thus, for example, acid addition salts of compounds of formula (I)are obtained by treatment with a suitable acid or a suitable ionexchanger reagent and salts with bases are obtained by treatment with asuitable base or with a suitable ion exchanger reagent. A salt is chosendepending on its tolerances for compound's use, such as agricultural orphysiological tolerance.

Salts of compounds of formula (I) can be converted in the customarymanner into the free compounds I, acid addition salts, for example, bytreatment with a suitable basic compound or with a suitable ionexchanger reagent and salts with bases, for example, by treatment with asuitable acid or with a suitable ion exchanger reagent.

Salts of compounds of formula (I) can be converted in a manner known perse into other salts of compounds of formula (I), acid addition salts,for example, into other acid addition salts, for example by treatment ofa salt of inorganic acid such as hydrochloride with a suitable metalsalt such as a sodium, barium or silver salt, of an acid, for examplewith silver acetate, in a suitable solvent in which an inorganic saltwhich forms, for example silver chloride, is insoluble and thusprecipitates from the reaction mixture.

Depending on the procedure or the reaction conditions, the compounds offormula (I), which have salt-forming properties can be obtained in freeform or in the form of salts.

Diastereomer mixtures or racemate mixtures of compounds of formula (I),in free form or in salt form, which can be obtained depending on whichstarting materials and procedures have been chosen can be separated in aknown manner into the pure diasteromers or racemates on the basis of thephysicochemical differences of the components, for example by fractionalcrystallization, distillation and/or chromatography.

Enantiomer mixtures, such as racemates, which can be obtained in asimilar manner can be resolved into the optical antipodes by knownmethods, for example by recrystallization from an optically activesolvent, by chromatography on chiral adsorbents, for examplehigh-performance liquid chromatography (HPLC) on acetyl cellulose, withthe aid of suitable microorganisms, by cleavage with specific,immobilized enzymes, via the formation of inclusion compounds, forexample using chiral crown ethers, where only one enantiomer iscomplexed, or by conversion into diastereomeric salts, for example byreacting a basic end-product racemate with an optically active acid,such as a carboxylic acid, for example camphor, tartaric or malic acid,or sulfonic acid, for example camphorsulfonic acid, and separating thediastereomer mixture which can be obtained in this manner, for exampleby fractional crystallization based on their differing solubilities, togive the diastereomers, from which the desired enantiomer can be setfree by the action of suitable agents, for example basic agents.

Pure diastereomers or enantiomers can be obtained according to theinvention not only by separating suitable isomer mixtures, but also bygenerally known methods of diastereoselective or enantioselectivesynthesis, for example by carrying out the process according to theinvention with starting materials of a suitable stereochemistry.

N-oxides can be prepared by reacting a compound of the formula (I) witha suitable oxidizing agent, for example the H₂O₂/urea adduct in thepresence of an acid anhydride, e.g. trifluoroacetic anhydride. Suchoxidations are known from the literature, for example from J. Med.Chem., 32 (12), 2561-73, 1989 or WO 00/15615 or C. White, Science, vol318, p. 783, 2007.

It can be advantageous to isolate or synthesize in each case thebiologically more effective isomer, for example enantiomer ordiastereomer, or isomer mixture, for example enantiomer mixture ordiastereomer mixture, if the individual components have a differentbiological activity.

The compounds of formula (I) and, where appropriate, the tautomersthereof, in each case in free form or in salt form, can, if appropriate,also be obtained in the form of hydrates and/or include other solvents,for example those which may have been used for the crystallization ofcompounds which are present in solid form.

Specific examples of compounds of formula (I) are illustrated in thefollowing Table P:

(I)

wherein R1 R2 R3 R4 R5 R6 R7 A1 A2 A3 A4 A5 P.1 H H H H

H CH3 N C—H C—H C—H N P.2 H H H H

H H C—CH3 C—CH3 C—H C—H C—H P.3 H H H H

H H N C—H C—H C—H N P.4 H H H H

H H C—CH3 C—H C—H C—CH3 C—H P.5 H H H H

H H C—CH3 C—H C—CH3 C—H C—H P.6 H H H H

H O—CH3 N C—H C—H C—H N P.7 H H H H

H H N C—H C—H C—H N P.8 H H H H

H H C—Cl C—H C—H C—CH3 C—H P.9 H H H H

H H C—CH3 C—H C—H C—CH3 C—H P.10 CH3 H H H

H H N C—H C—H C—H C—H P.11 H H H H

H H C—Cl C—H C—Cl C—H C—H P.12 H H H H

H H C—Cl C—H C—H C—H N P.13 H H H H

H H C—Cl C—H C—CH3 C—H C—H P.14 H H H H

H allyl N C—H C—H C—H N P.15 H H H H

H H C—CF3 C—H C—H C—H N P.16 F F H H

H H N C—H C—H C—H N P.17 H H H H

H H C—CF3 C—H C—H C—H N P.18 H H H H

H C(═O)—CH3 N C—H C—H C—H N P.19 H H H H

H H N C—H C—H C—H N P.20 H H H H

H H C—CH3 C—Cl C—H C—H C—H P.21 H H H H

H H C—CH3 C—H C—H C—H N P.22 H H H H

H propargyl N C—H C—H C—H N P.23 H H H H

H H C—Cl C—H C—H C—H N P.24 H H H H

H H C—CF3 C—H C—H C—H N P.25 H H H H

H H C—CH3 C—H C—H C—H N P.26 H H H H

H H C—CF3 C—H C—H C—H N P.27 H H H H

H H C—CH3 C—H C—Cl C—H C—H P.28 H H H H

CH3 H N C—H C—H C—H N P.29 H H H H

H H C—Cl C—H C—H C—H N P.30 H H H H

H H C—Cl C—CH3 C—H C—H C—H P.31 H H H H

H H N C—H C—H C—H N P.32 H H H H

H H C—CH3 C—CH3 C—H C—H C—H P.33 H H H H

H CH2—O—CH3 N C—H C—H C—H N P.34 H H H H

CH3 H C—CH3 C—H C—H C—CH3 C—H P.35 H H H H

H H C—CH3 C—H C—H C—CH3 C—H P.36 H H H H

H H C—CH3 C—H C—CH3 C—H C—H P.37 H H H H

H H C—Cl C—H C—H C—H N P.38 H H H H

H H C—CH3 C—CH3 C—H C—H C—H P.39 H H H H

H H C—CH3 C—H C—H C—CH3 C—H P.40 F H H H

H H C—CH3 C—H C—H C—CH3 C—H P.41 H H H H

H H C—CH3 C—H C—H C—CH3 C—H P.42 H H H H

H H N C—H C—H C—H N P.43 H H H H

H H C—CH3 C—H C—H C—H N P.44 H H H H

H H C—CH3 C—H C—CH3 C—H C—H P.45 H H H H

H H C—CH3 C—H C—H C—Cl C—H P.46 H H H H

H H C—CH3 C—H C—CH3 C—H C—H P.47 H H H H

H H C—CH3 C—H C—H C—H N P.48 H H H H

H CN N C—H C—H C—H N P.49 H H H H

H H C—Cl C—H C—H C—H N P.50 H H H H

CH3 H N C—H C—H C—H N P.51 H H H H

H O—C(═O)—CH3 N C—H C—H C—H N P.52 H H H H

H H N C—H C—H C—H N P.53 H H H H

H H C—CH3 C—H C—H C—CH3 C—H P.54 H H H H

H H C—Cl C—H C—H C—Cl C—H P.55 H H H H

H OH N C—H C—H C—H N P.56 H H H H

H H C—Cl C—H C—H C—H N P.57 H H H H

H H C—CH3 C—CH3 C—H C—H C—H P.58 H H H H

H H C—CH3 C—H C—CH3 C—H C—H P.59 H H H H

H H C—CH3 C—CH3 C—H C—H C—H P.60 H H H H

H H C—CF3 C—H C—H C—H N P.61 H H H H

H H C—CH3 C—H C—H C—H N P.62 H H H H

H benzyl N C—H C—H C—H N P.63 H H H H

H H C—CH3 C—H C—H C—H N P.64 H H H H

H H C—Cl C—Cl C—H C—H C—H P.65 H H H H

H H C—F C—H C—H C—H N P.66 H H H H

H H C—Cl C—H C—H C—H N P.67 H H H H

H H C—F C—H C—H C—H N P.68 H H H H

H H C—Cl C—H C—H C—H N P.69 H H H H

H H C—Cl C—H C—H C—H N P.70 H H H H

H H C—F C—H C—H C—H N P.71 H H H H

H H C—F C—H C—H C—H N P.72 H H H H

H H C—Cl C—H C—H C—H N P.73 H H H H

H cyclo- propanecarbonyl C—Cl C—H C—H C—H N P.74 H H H H

H cyclo- propoxycarbonyl C—Cl C—H C—H C—H N P.75 H H H H

H H C—F C—H C—H C—H N P.76 H H H H

H H N C—H C—H C—H N P.77 H H H H

H H C—Cl C—H C—H C—H N P.78 H H H H

H H N C—H C—H C—H N P.79 H H H H

H H C—F C—H C—H C—H N P.80 H H H H

H H N C—H C—H C—H N P.81 H H H H

H H C—Cl C—H C—H C—H N P.82 H H H H

H H N C—H C—H C—H N P.83 H H H H

H H C—F C—H C—H C—H N P.84 H H H H

H H C—Cl C—H C—H C—H N P.85 H H H H

H H C—Cl C—H C—H C—H N P.86 H H H H

H H C—Cl C—H C—H C—H N P.87 H H H H

H H C—CF3 C—H C—H C—H N P.88 H H H H

H H N C—H C—H C—H N P.89 H H H H

H H N C—H C—H C—H N P.90 H H H H

H H C—Cl C—H C—H C—H N P.91 H H H H

H H C—CF3 C—H C—H C—H N P.92 H H H H

H H C—Cl C—H C—H C—H N P.93 H H H H

H H C—CF3 C—H C—H C—H N P.94 H H H H

H H C—Cl C—H C—H C—H N P.95 H H H H

H H C—F C—H C—H C—H N P.96 H H H H

H H C—F C—H C—H C—H N P.97 H H H H

H H C—Br C—H C—H C—H N P.98 H H H H

H H C—Br C—H C—H C—H N P.99 H H H H

H H C—CF3 C—H C—H C—H N P.100 H H H H

H H C—F C—H C—H C—H N P.101 H H H H

H H C—CF3 C—H C—H C—H N P.102 H H H H

H H C—F C—H C—H C—H N P.103 H H H H

H H C—Cl C—H C—H C—H N P.104 H H H H

H H C—CF3 C—H C—H C—H N P.105 H H H H

H H C—CF3 C—H C—H C—H N P.106 H H H H

H H C—CF3 C—H C—H C—H N P.107 H H H H

H H C—Cl C—H C—H C—H N P.108 H H H H

H H C—F C—H C—H C—H N P.109 H H H H

H H C—Cl C—H C—H C—H N P.110 H H H H

H H C—Br C—H C—H C—H N P.111 H H H H

H H N C—CF3 C—H C—H C—H P.112 H H H H

H H C—Cl C—H C—H C—H N P.113 H H H H

H H C—Br C—H C—H C—H N P.114 H H H H

H H C—CF3 C—H C—H C—H N P.115 H H H H

H H C—Cl C—H C—H C—H N P.116 H H H H

H H C—Br C—H C—H C—H N P.117 H H H H

H H C—F C—H C—H C—H N P.118 H H H H

H H C—CF3 C—H C—H C—H N P.119 H H H H

H H C—Cl C—H C—H C—H N P.120 H H H H

H H C—F C—H C—H C—H N P.121 H H H H

H H C—F C—H C—H C—H N P.122 H H H H

H H C—F C—H C—H C—H N P.123 H H H H

H H C—F C—H C—H C—H N P.124 H H H H

H H C—CF3 C—H C—H C—H N P.125 H H H H

H H C—F C—H C—H C—H N P.126 H H H H

H H C—F C—H C—H C—H N P.127 H H H H

H H C—CF3 C—H C—H C—H N P.128 H H H H

H H C—CF3 C—H C—H C—H N P.129 H H H H

H H C—CF3 C—H C—H C—H N P.130 H H H H

H H C—CF3 C—H C—H C—H N P.131 H H H H

H H C—CF3 N C—H C—H C—H P.132 H H H H

H H C—F C—H C—H C—H C—F P.133 H H H H

H H C—CF3 C—H C—H C—H C—H P.134 H H H H

H H C—CF3 C—H C—H C—H C—H P.135 H H H H

H H C—CF3 C—H C—H C—H C—H P.136 H H H H

H H C—Cl N C—H C—H N P.137 H H H H

H H C—CF3 C—H C—H C—H C—H P.138 H H H H

H H C—Cl N C—H C—H N P.139 H H H H

H H C—Cl N C—H C—H N P.140 H H H H

H H C—CF3 C—H C—H C—H C—H P.141 H H H H

H H C—F C—H C—H C—H C—F P.142 H H H H

H H C—F C—H C—H C—H C—F P.143 H H H H

H H C—CF3 C—H C—H C—H C—H P.144 H H H H

H H C—F C—H C—H C—H C—F P.145 H H H H

H H C—CF3 C—H C—H C—H C—H P.146 H H H H

H H C—CF3 C—H C—H C—H C—H P.147 H H H H

H H C—Cl C—H N C—H N P.148 H H H H

H H C—Cl C—H N C—H N P.149 H H H H

H H C—CF3 C—H C—H C—H C—H P.150 H H H H

H H C—CF3 N C—H C—H C—H P.151 H H H H

H H C—Cl N C—H C—H N P.152 H H H H

H H C—CF3 C—H C—H C—H C—H P.153 H H H H

H H C—CF3 N C—H C—H C—H P.154 H H H H

H H C—Cl N C—H C—H N P.155 H H H H

H H C—Cl C—H N C—H N P.156 H H H H

H H C—F C—H C—H C—H C—F P.157 H H H H

H H C—CF3 C—H C—H C—H C—H P.158 H H H H

H H C—CF3 C—H C—H C—H C—H P.159 H H H H

H H C—S—CH3 C—H C—H C—H N P.160 H H H H

H H C—SO2—CH3 C—H C—H C—H N P.161 H H H H

H H C—SO—CH3 C—H C—H C—H N P.162 H H H H

H H C—CF3 N C—H C—H C—H P.163 H H H H

H H C—F C—H C—H C—H C—F P.164 H H H H

H H C—Cl N C—H C—H N P.165 H H H H

H H C—Cl C—H N C—H N P.166 H H H H

H H C—Cl C—H N C—H N P.167 H H H H

H H C—Cl C—H N C—H N P.168 H H H H

H H C—CF3 C—H C—H C—H C—H P.169 H H H H

H H C—Br N C—H C—H C—H P.170 H H H H

H H C—F N C—H C—H C—H P.171 H H H H

H H C—F C—H C—H C—H C—F P.172 H H H H

H H C—CF3 C—H C—H C—H C—H P.173 H H H H

H H C—CF3 C—H N C—H N P.174 H H H H

H H C—CF3 N C—H N C—H P.175 H H H H

H H C—CF3 C—H C—H N N P.176 H H H H

H H C—CF3 N N C—H C—H P.177 H H H H

H H C—CF3 C—H N N C—H P.178 H H H H

H H C—CF3 N C—H C—H N P.179 H H H H

H H C—CF3 C—H N C—H N P.180 H H H H

H H C—CF3 N C—H N C—H P.181 H H H H

H H C—CF3 C—H C—H C—H N P.182 H H H H

H H C—Cl C—H C—H C—H N P.183 H H H H

H H C—CF3 N C—H C—H C—H P.184 H H H H

H H C—CF3 N C—H C—H N P.185 H H H H

H H C—CF3 C—H C—H C—H N P.186 H H H H

H H C—Cl C—H C—H C—H N P.187 H H H H

H H C—CF3 C—H C—H C—H N P.188 Me H H H

H H C—CF3 C—H C—H C—H N P.189 H H H H

H H C—CF3 C—H C—H C—H N P.190 H H H H

Me H C—CF3 C—H C—H C—H N P.191 H H H H

H H C—CF3 C—H C—H C—H N

A compound of formula (I) has been found to control the damage caused bya pest and/or fungi.

In an embodiment, a compound of formula (I) can be used in agriculture.

Accordingly, the invention is moreover directed to a method ofcontrolling damage and/or yield loss caused by a pest and/or fungi whichcomprises applying to a pest, to a locus of a pest, or to a plantsusceptible to attack by a pest and/or fungi or to a plant propagationmaterial an effective amount of a compound of formula (I).

The compounds according to the invention can be used for controlling,i.e. containing or destroying, pests and/or fungi which occur inparticular on plants, especially on useful plants and ornamentals inagriculture, in horticulture and in forests, or on organs, such asfruits, flowers, foliage, stalks, tubers, seeds or roots, of suchplants, and in some cases even plant organs which are formed at a laterpoint in time remain protected against these pests.

The compounds of formula (I) according to the invention are preventivelyand/or curatively valuable active ingredients in the field of pestcontrol, even at low rates of application, which can be used againstpesticide resistant pests and fungi, which compounds of formula (I) havea very favorable biocidal spectrum and are well tolerated bywarm-blooded species, fish and plants.

The compounds according to the invention act against all or individualdevelopmental stages of normally sensitive, but also resistant, animalpests, such as insects or representatives of the order Acarina. Theinsecticidal or acaricidal activity of the compounds according to theinvention can manifest itself directly, i.e. in destruction of thepests, which takes place either immediately or only after some time haselapsed, for example during ecdysis, or indirectly, for example in areduced oviposition and/or hatching rate, a good activity correspondingto a destruction rate (mortality) of at least 50 to 60%.

Examples of the above mentioned animal pests are:

from the order Acarina, for example,

Acalitus spp, Aculus spp, Acaricalus spp, Aceria spp, Acarus siro,Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobiaspp, Calipitrimerus spp., Chorioptes spp., Dermanyssus gallinae,Dermatophagoides spp, Eotetranychus spp, Eriophyes spp., Hemitarsonemusspp, Hyalomma spp., Ixodes spp., Olygonychus spp, Ornithodoros spp.,Polyphagotarsone latus, Panonychus spp., Phyllocoptruta oleivora,Phytonemus spp, Polyphagotarsonemus spp, Psoroptes spp., Rhipicephalusspp., Rhizoglyphus spp., Sarcoptes spp., Steneotarsonemus spp,Tarsonemus spp. and Tetranychus spp.;

from the order Anoplura, for example,

Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp. andPhylloxera spp.;

from the order Coleoptera, for example,

Agriotes spp., Amphimallon majale, Anomala orientalis, Anthonomus spp.,Aphodius spp, Astylus atromaculatus, Ataenius spp, Atomaria linearis,Chaetocnema tibialis, Cerotoma spp, Conoderus spp, Cosmopolites spp.,Cotinis nitida, Curculio spp., Cyclocephala spp, Dermestes spp.,Diabrotica spp., Diloboderus abderus, Epilachna spp., Eremnus spp.,Heteronychus arator, Hypothenemus hampei, Lagria vilosa, LeptinotarsadecemLineata, Lissorhoptrus spp., Liogenys spp, Maecolaspis spp,Maladera castanea, Megascelis spp, Melighetes aeneus, Melolontha spp.,Myochrous armatus, Orycaephilus spp., Otiorhynchus spp., Phyllophagaspp, Phlyctinus spp., Popillia spp., Psylliodes spp., Rhyssomatusaubtilis, Rhizopertha spp., Scarabeidae, Sitophilus spp., Sitotrogaspp., Somaticus spp, Sphenophorus spp, Sternechus subsignatus, Tenebriospp., Tribolium spp. and Trogoderma spp.;

from the order Diptera, for example,

Aedes spp., Anopheles spp, Antherigona soccata, Bactrocea oleae, Bibiohortulanus, Bradysia spp, Calliphora erythrocephala, Ceratitis spp.,Chrysomyia spp., Culex spp., Cuterebra spp., Dacus spp., Delia spp,Drosophila melanogaster, Fannia spp., Gastrophilus spp., Geomyzatripunctata, Glossina spp., Hypoderma spp., Hyppobosca spp., Liriomyzaspp., Lucilia spp., Melanagromyza spp., Musca spp., Oestrus spp.,Orseolia spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp.,Rhagoletis spp, Rivelia quadrifasciata, Scatella spp, Sciara spp.,Stomoxys spp., Tabanus spp., Tannia spp. and Tipula spp.;

from the order Hemiptera, for example,

Acanthocoris scabrator, Acrosternum spp, Adelphocoris lineolatus,Amblypelta nitida, Bathycoelia thalassina, Blissus spp, Cimex spp.,Clavigralla tomentosicollis, Creontiades spp, Distantiella theobroma,Dichelops furcatus, Dysdercus spp., Edessa spp, Euchistus spp., Eurydemapulchrum, Eurygaster spp., Halyomorpha halys, Horcias nobilellus,Leptocorisa spp., Lygus spp, Margarodes spp, Murgantia histrionic,Neomegalotomus spp, Nesidiocoris tenuis, Nezara spp., Nysius simulans,Oebalus insularis, Piesma spp., Piezodorus spp, Rhodnius spp.,Sahlbergella singularis, Scaptocoris castanea, Scotinophara spp.,Thyanta spp, Triatoma spp., Vatiga illudens;

from the order homoptera, for example,

Acyrthosium pisum, Adalges spp, Agalliana ensigera, Agonoscenatargionii, Aleurodicus spp, Aleurocanthus spp, Aleurolobus barodensis,Aleurothrixus floccosus, Aleyrodes brassicae, Amarasca biguttula,Amritodus atkinsoni, Aonidiella spp., Aphididae, Aphis spp., Aspidiotusspp., Aulacorthum solani, Bactericera cockerelli, Bemisia spp,Brachycaudus spp, Brevicoryne brassicae, Cacopsylla spp, Cavariellaaegopodii Scop., Ceroplaster spp., Chrysomphalus aonidium, Chrysomphalusdictyospermi, Cicadella spp, Cofana spectra, Cryptomyzus spp, Cicadulinaspp, Coccus hesperidum, Dalbulus maidis, Dialeurodes spp, Diaphorinacitri, Diuraphis noxia, Dysaphis spp, Empoasca spp., Eriosoma larigerum,Erythroneura spp., Gascardia spp., Glycaspis brimblecombei, Hyadaphispseudobrassicae, Hyalopterus spp, Hyperomyzus pallidus, Idioscopusclypealis, Jacobiasca lybica, Laodelphax spp., Lecanium corni,Lepidosaphes spp., Lopaphis erysimi, Lyogenys maidis, Macrosiphum spp.,Mahanarva spp, Metcalfa pruinosa, Metopolophium dirhodum, Myndus crudus,Myzus spp., Neotoxoptera sp, Nephotettix spp., Nilaparvata spp.,Nippolachnus piri Mats, Odonaspis ruthae, Oregma lanigera Zehnter,Parabemisia myricae, Paratrioza cockerelli, Parlatoria spp., Pemphigusspp., Peregrinus maidis, Perkinsiella spp, Phorodon humuli, Phylloxeraspp, Planococcus spp., Pseudaulacaspis spp., Pseudococcus spp.,Pseudatomoscelis seriatus, Psylla spp., Pulvinaria aethiopica,Quadraspidiotus spp., Quesada gigas, Recilia dorsalis, Rhopalosiphumspp., Saissetia spp., Scaphoideus spp., Schizaphis spp., Sitobion spp.,Sogatella furcifera, Spissistilus festinus, Tarophagus Proserpina,Toxoptera spp, Trialeurodes spp, Tridiscus sporoboli, Trionymus spp,Trioza erytreae, Unaspis citri, Zygina flammigera, Zyginidiascutellaris,

from the order Hymenoptera, for example,

Acromyrmex, Arge spp, Atta spp., Cephus spp., Diprion spp., Diprionidae,Gilpinia polytoma, Hoplocampa spp., Lasius spp., Monomorium pharaonis,Neodiprion spp., Pogonomyrmex spp, Slenopsis invicta, Solenopsis spp.and Vespa spp.;

from the order Isoptera, for example,

Coptotermes spp, Corniternes cumulans, Incisitermes spp, Macrotermesspp, Mastotermes spp, Microtermes spp, Reticulitermes spp.; Solenopsisgeminate

from the order Lepidoptera, for example,

Acleris spp., Adoxophyes spp., Aegeria spp., Agrotis spp., Alabamaargillaceae, Amylois spp., Anticarsia gemmatalis, Archips spp.,Argyresthia spp, Argyrotaenia spp., Autographa spp., Bucculatrixthurberiella, Busseola fusca, Cadra cautella, Carposina nipponensis,Chilo spp., Choristoneura spp., Chrysoteuchia topiaria, Clysiaambiguella, Cnaphalocrocis spp., Cnephasia spp., Cochylis spp.,Coleophora spp., Colias lesbia, Cosmophila flava, Crambus spp,Crocidolomia binotalis, Cryptophlebia leucotreta, Cydalima perspectalis,Cydia spp., Diaphania perspectalis, Diatraea spp., Diparopsis castanea,Earias spp., Eldana saccharina, Ephestia spp., Epinotia spp, Estigmeneacrea, Etiella zinckinella, Eucosma spp., Eupoecilia ambiguella,Euproctis spp., Euxoa spp., Feltia jaculiferia, Grapholita spp., Hedyanubiferana, Heliothis spp., Hellula undalis, Herpetogramma spp,Hyphantria cunea, Keiferia lycopersicella, Lasmopalpus lignosellus,Leucoptera scitella, Lithocollethis spp., Lobesia botrana, Loxostegebifidalis, Lymantria spp., Lyonetia spp., Malacosoma spp., Mamestrabrassicae, Manduca sexta, Mythimna spp, Noctua spp, Operophtera spp.,Orniodes indica, Ostrinia nubilalis, Pammene spp., Pandemis spp.,Panolis flammea, Papaipema nebris, Pectinophora gossypiela,Perileucoptera coffeella, Pseudaletia unipuncta, Phthorimaeaoperculella, Pieris rapae, Pieris spp., Plutella xylostella, Prays spp.,Pseudoplusia spp, Rachiplusia nu, Richia albicosta, Scirpophaga spp.,Sesamia spp., Sparganothis spp., Spodoptera spp., Sylepta derogate,Synanthedon spp., Thaumetopoea spp., Tortrix spp., Trichoplusia ni, Tutaabsoluta, and Yponomeuta spp.;

from the order Mallophaga, for example,

Damalinea spp. and Trichodectes spp.;

from the order Orthoptera, for example,

Blatta spp., Blattella spp., Gryllotalpa spp., Leucophaea maderae,Locusta spp., Neocurtilla hexadactyla, Periplaneta spp., Scapteriscusspp, and Schistocerca spp.;

from the order Psocoptera, for example,

Liposcelis spp.;

from the order Siphonaptera, for example,

Ceratophyllus spp., Ctenocephalides spp. and Xenopsylla cheopis;

from the order Thysanoptera, for example,

Calliothrips phaseoli, Frankliniella spp., Heliothrips spp,Hercinothrips spp., Parthenothrips spp, Scirtothrips aurantii,Sericothrips variabilis, Taeniothrips spp., Thrips spp;

-   -   from the order Thysanura, for example,        Lepisma saccharina.

In a further aspect, the invention may also relate to a method ofcontrolling or preventing infestation of useful plants byphytopathogenic microorganisms, wherein a compound of formula (I) isapplied as active ingredient to the plants, to parts thereof or thelocus thereof. The compounds of formula (I) according to the inventionare distinguished by activity, by being well tolerated by plants and bybeing environmentally safe. They have very useful curative, preventiveand systemic properties and are used for protecting numerous usefulplants. The compounds of formula (I) can be used to inhibit or destroythe diseases that occur on plants or parts of plants (fruit, blossoms,leaves, stems, tubers, roots) of different useful plants, while at thesame time protecting also those parts of the plants that grow later e.g.from phytopathogenic microorganisms. It is also possible to usecompounds of formula (I) as dressing agents for the treatment of plantpropagation material, in particular of seeds (fruit, tubers, grains) andplant cuttings (e.g. rice), for the protection against fungal infectionsas well as against phytopathogenic fungi occurring in the soil.

Examples of fungi include: Fungi imperfecti (e.g. Botrytis, Pyricularia,Helminthosporium, Fusarium, Septoria, Cercospora and Alternaria);Basidiomycetes (e.g. Rhizoctonia, Hemileia, Puccinia); the Ascomycetesclasses (e.g. Venturia and Erysiphe, Podosphaera, Monilinia, Uncinula);Oomycetes classes (e.g. Phytophthora, Pythium, Plasmopara); Zygomycetes(e.g., Rhizopus spp.); family Phakopsoraceae, particularly those of thegenus Phakopsora, for example Phakopsora pachyrhizi, which is alsoreferred to as Asian soybean rust, and those of the family Pucciniaceae,particularly those of the genus Puccinia such as Puccinia graminis, alsoknown as stem rust or black rust, which is a problem disease in cerealplants and Puccinia recondita, also known as brown rust.

Among the plants and the possible diseases of these plants protected bythe method according to the present invention, mention may be made of:

wheat, as regards controlling the following seed diseases: fusaria(Microdochium nivale and Fusarium roseum), stinking smut (Tilletiacaries, Tilletia controversa or Tilletia indica), septoria disease(Septoria nodorum) and loose smut;

wheat, as regards controlling the following diseases of the aerial partsof the plant: cereal eyespot (Tapesia yallundae, Tapesia acuiformis),take-all (Gaeumannomyces graminis), foot blight (F. culmorum, F.graminearum), black speck (Rhizoctonia cerealis), powdery mildew(Erysiphe graminis form a specie tritici), rusts (Puccinia striiformisand Puccinia recondita) and septoria diseases (Septoria tritici andSeptoria nodorum);

wheat and barley, as regards controlling bacterial and viral diseases,for example barley yellow mosaic; —barley, as regards controlling thefollowing seed diseases: net blotch (Pyrenophora graminea, Pyrenophorateres and Cochliobolus sativus), loose smut (Ustilago nuda) and fusaria(Microdochium nivale and Fusarium roseum);

barley, as regards controlling the following diseases of the aerialparts of the plant: cereal eyespot (Tapesia yallundae), net blotch(Pyrenophora teres and Cochliobolus sativus), powdery mildew (Erysiphegraminis form a specie hordei), dwarf leaf rust (Puccinia hordei) andleaf blotch (Rhynchosporium secalis);

potato, as regards controlling tuber diseases (in particularHelminthosporium solani, Phoma tuberosa, Rhizoctonia solani, Fusariumsolani), mildew (Plrytopthora infestans) and certain viruses (virus Y);

potato, as regards controlling the following foliage diseases: earlyblight (Alternaria solani), mildew (Phytophthora infestans);

cotton, as regards controlling the following diseases of young plantsgrown from seeds: damping-off and collar rot (Rhizoctonia solani,Fusarium oxysporum) and black root rot (Thielaviopsis basicola);

protein yielding plants, for example peas, as regards controlling thefollowing seed diseases: anthracnose (Ascochyta pisi, Mycosphaerellapinodes), fusaria (Fusarium oxysporum), grey mould (Botrytis cinerea)and mildew (Peronospora pisi);

oil-bearing plants, for example rape, as regards controlling thefollowing seed diseases: Phoma lingam, Alternaria brassicae andSclerotinia sclerotiorum;

corn, as regards controlling seed diseases: (Rhizopus sp., Penicilliumsp.,

Trichoderma sp., Aspergillus sp., and Gibber ellafujikuroi);

flax, as regards controlling the seed disease: Alternaria linicola;

forest trees, as regards controlling damping-off (Fusarium oxysporum,Rhizoctonia solani);

rice, as regards controlling the following diseases of the aerial parts:blast disease (Magnaporthe grisea), bordered sheath spot (Rhizoctoniasolani);

leguminous plants, as regards controlling the following diseases ofseeds or of young plants grown from seeds: damping-off and collar rot(Fusarium oxysporum, Fusarium roseum, Rhizoctonia solani, Pythium sp.);

leguminous plants, as regards controlling the following diseases of theaerial parts: grey mould (Botrytis sp.), powdery mildews (in particularErysiphe cichoracearum, Sphaerotheca fuliginea and Leveillula taurica),fusaria (Fusarium oxysporum, Fusarium roseum), leaf spot (Cladosporiumsp.), alternaria leaf spot (Alternaria sp.), anthracnose (Colletotrichumsp.), septoria leaf spot (Septoria sp.), black speck (Rhizoctoniasolani), mildews (for example Bremia lactucae, Peronospora sp.,Pseudoperonospora sp., Phytophthora sp.);

fruit trees, as regards diseases of the aerial parts: monilia disease(Monilia fructigenae, M. laxa), scab (Venturia inaequalis), powderymildew (Podosphaera leucotricha); —vine, as regards diseases of thefoliage: in particular grey mould (Botrytis cinerea), powdery mildew(Uncinula necator), black rot (Guignardia biwelli) and mildew(Plasmopara viticola);

beetroot, as regards the following diseases of the aerial parts:cercospora blight (Cercospora beticola), powdery mildew (Erysiphebeticola), leaf spot (Ramularia beticola).

The fungicide composition according to the present invention may also beused against fungal diseases liable to grow on or inside timber. Theterm “timber” means all types of species of wood, and all types ofworking of this wood intended for construction, for example solid wood,high-density wood, laminated wood, and plywood. The method for treatingtimber according to the invention mainly consists in contacting one ormore compounds of the present invention, or a composition according tothe invention; this includes for example direct application, spraying,dipping, injection or any other suitable means.

In a further aspect, the invention also relates to a method ofcontrolling damage to plant and parts thereof by plant parasiticnematodes (Endoparasitic-, Semiendoparasitic- and Ectoparasiticnematodes), especially plant parasitic nematodes such as root knotnematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogynejavanica, Meloidogyne arenaria and other Meloidogyne species;cyst-forming nematodes, Globodera rostochiensis and other Globoderaspecies; Heterodera avenae, Heterodera glycines, Heterodera schachtii,Heterodera trifolii, and other Heterodera species; Seed gall nematodes,Anguina species; Stem and foliar nematodes, Aphelenchoides species;Sting nematodes, Eelonolaimus longicaudatus and other Belonolaimusspecies; Pine nematodes, Bursaphelenchus xylophilus and otherBursaphelenchus species; Ring nematodes, Criconema species, Criconemellaspecies, Criconemoides species, Mesocriconema species; Stem and bulbnematodes, Ditylenchus destructor, Ditylenchus dipsaci and otherDitylenchus species; Awl nematodes, Dolichodorus species; Spiralnematodes, Heliocotylenchus multicinctus and other Helicotylenchusspecies; Sheath and sheathoid nematodes, Hemicycliophora species andHemicriconemoides species; Hirshmanniella species; Lance nematodes,Hoploaimus species; false rootknot nematodes, Nacobbus species; Needlenematodes, Longidorus elongatus and other Longidorus species; Pinnematodes, Pratylenchus species; Lesion nematodes, Pratylenchusneglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchusgoodeyi and other Pratylenchus species; Burrowing nematodes, Radopholussimilis and other Radopholus species; Reniform nematodes, Rotylenchusrobustus, Rotylenchus reniformis and other Rotylenchus species;Scutellonema species; Stubby root nematodes, Trichodorus primitivus andother Trichodorus species, Paratrichodorus species; Stunt nematodes,Tylenchorhynchus claytoni, Tylenchorhynchus dubius and otherTylenchorhynchus species; Citrus nematodes, Tylenchulus species; Daggernematodes, Xiphinema species; and other plant parasitic nematodespecies, such as Subanguina spp., Hypsoperine spp., Macroposthonia spp.,Melinius spp., Punctodera spp., and Quinisulcius spp.

The compounds of the invention may also have activity against themolluscs. Examples of which include, for example, Ampullariidae; Arion(A. ater, A. circumscriptus, A. hortensis, A. rufus); Bradybaenidae(Bradybaena fruticum); Cepaea (C. hortensis, C. Nemoralis); ochlodina;Deroceras (D. agrestis, D. empiricorum, D. laeve, D. reticulatum);Discus (D. rotundatus); Euomphalia; Galba (G. trunculata); Helicelia (H.itala, H. obvia); Helicidae Helicigona arbustorum); Helicodiscus; Helix(H. aperta); Limax (L. cinereoniger, L. flavus, L. marginatus, L.maximus, L. tenellus); Lymnaea; Milax (M. gagates, M. marginatus, M.sowerbyi); Opeas; Pomacea (P. canaticulata); Vallonia and Zanitoides.The combinations according to the present invention are particularlyeffective against Deroceras, such as Deroceras reticulatum.

In an embodiment, independent of other embodiments, the compounds offormula (I) are especially useful for the control of nematodes.Particularly, the nematode species Meloidogyne spp., Heterodera spp.,Rotylenchus spp. and Pratylenchus spp. can be controlled by compounds ofthe invention.

Compounds of this invention are effective for controlling nematode,insect, acarid pests and/or fungal pathogens of agronomic plants, bothgrowing and harvested, when employed alone, they may also be used incombination with other biological active agents used in agriculture,such as one or more nematicides, insecticides, acaricides, fungicides,bactericides, plant activator, molluscicide, and pheromones (whetherchemical or biological). Mixing the compounds of the invention or thecompositions thereof in the use form as pesticides with other pesticidesfrequently results in a broader pesticidal spectrum of action. Forexample, the formula (I) compounds of this invention may be usedeffectively in conjunction or combination with pyrethroids,neonicotinoids, macrolides, diamides, phosphates, carbamates,cyclodienes, formamidines, phenol tin compounds, chlorinatedhydrocarbons, benzoylphenyl ureas, pyrroles and the like.

The activity of the compositions according to the invention can bebroadened considerably, and adapted to prevailing circumstances, byadding, for example, one or more insecticidally, acaricidally,nematicidally and/or fungicidally active agents. The combinationscompounds of formula (I) with other insecticidally, acaricidally,nematicidally and/or fungicidally active agents may also have furthersurprising advantages which can also be described, in a wider sense, assynergistic activity. For example, better tolerance by plants, reducedphytotoxicity, pests or fungi can be controlled in their differentdevelopment stages or better behaviour during their production, forexample during grinding or mixing, during their storage or during theiruse.

The following list of pesticides together with which the compoundsaccording to the invention can be used, is intended to illustrate thepossible combinations by way of example.

The following combination of the compounds of formula (I) with anotheractive compounds are preferred (the abbreviation “TX” means “onecompound selected from the compounds of formulae P.1 to P.191 describedin Table P of the present invention”):

an adjuvant selected from the group of substances consisting ofpetroleum oils (alternative name) (628)+TX,

an acaricide selected from the group of substances consisting of1,1-bis(4-chlorophenyl)-2-ethoxyethanol (IUPAC name) (910)+TX,2,4-dichlorophenyl benzenesulfonate (IUPAC/Chemical Abstracts name)(1059)+TX, 2-fluoro-N-methyl-N-1-naphthylacetamide (IUPAC name)(1295)+TX, 4-chlorophenyl phenyl sulfone (IUPAC name) (981)+TX,abamectin (1)+TX, acequinocyl (3)+TX, acetoprole [CCN]+TX, acrinathrin(9)+TX, aldicarb (16)+TX, aldoxycarb (863)+TX, alpha-cypermethrin(202)+TX, amidithion (870)+TX, amidoflumet [CCN]+TX, amidothioate(872)+TX, amiton (875)+TX, amiton hydrogen oxalate (875)+TX, amitraz(24)+TX, aramite (881)+TX, arsenous oxide (882)+TX, AVI 382 (compoundcode)+TX, AZ 60541 (compound code)+TX, azinphos-ethyl (44)+TX,azinphos-methyl (45)+TX, azobenzene (IUPAC name) (888)+TX, azocyclotin(46)+TX, azothoate (889)+TX, benomyl (62)+TX, benoxafos (alternativename) [CCN]+TX, benzoximate (71)+TX, benzyl benzoate (IUPAC name)[CCN]+TX, bifenazate (74)+TX, bifenthrin (76)+TX, binapacryl (907)+TX,brofenvalerate (alternative name)+TX, bromocyclen (918)+TX, bromophos(920)+TX, bromophos-ethyl (921)+TX, bromopropylate (94)+TX, buprofezin(99)+TX, butocarboxim (103)+TX, butoxycarboxim (104)+TX, butylpyridaben(alternative name)+TX, calcium polysulfide (IUPAC name) (111)+TX,camphechlor (941)+TX, carbanolate (943)+TX, carbaryl (115)+TX,carbofuran (118)+TX, carbophenothion (947)+TX, CGA 50′439 (developmentcode) (125)+TX, chinomethionat (126)+TX, chlorbenside (959)+TX,chlordimeform (964)+TX, chlordimeform hydrochloride (964)+TX,chlorfenapyr (130)+TX, chlorfenethol (968)+TX, chlorfenson (970)+TX,chlorfensulphide (971)+TX, chlorfenvinphos (131)+TX, chlorobenzilate(975)+TX, chloromebuform (977)+TX, chloromethiuron (978)+TX,chloropropylate (983)+TX, chlorpyrifos (145)+TX, chlorpyrifos-methyl(146)+TX, chlorthiophos (994)+TX, cinerin I (696)+TX, cinerin II(696)+TX, cinerins (696)+TX, clofentezine (158)+TX, closantel(alternative name) [CCN]+TX, coumaphos (174)+TX, crotamiton (alternativename) [CCN]+TX, crotoxyphos (1010)+TX, cufraneb (1013)+TX, cyanthoate(1020)+TX, cyflumetofen (CAS Reg. No.: 400882-07-7)+TX, cyhalothrin(196)+TX, cyhexatin (199)+TX, cypermethrin (201)+TX, DCPM (1032)+TX, DDT(219)+TX, demephion (1037)+TX, demephion-O (1037)+TX, demephion-S(1037)+TX, demeton (1038)+TX, demeton-methyl (224)+TX, demeton-O(1038)+TX, demeton-O-methyl (224)+TX, demeton-S (1038)+TX,demeton-S-methyl (224)+TX, demeton-S-methylsulphon (1039)+TX,diafenthiuron (226)+TX, dialifos (1042)+TX, diazinon (227)+TX,dichlofluanid (230)+TX, dichlorvos (236)+TX, dicliphos (alternativename)+TX, dicofol (242)+TX, dicrotophos (243)+TX, dienochlor (1071)+TX,dimefox (1081)+TX, dimethoate (262)+TX, dinactin (alternative name)(653)+TX, dinex (1089)+TX, dinex-diclexine (1089)+TX, dinobuton(269)+TX, dinocap (270)+TX, dinocap-4 [CCN]+TX, dinocap-6 [CCN]+TX,dinocton (1090)+TX, dinopenton (1092)+TX, dinosulfon (1097)+TX,dinoterbon (1098)+TX, dioxathion (1102)+TX, diphenyl sulfone (IUPACname) (1103)+TX, disulfuram (alternative name) [CCN]+TX, disulfoton(278)+TX, DNOC (282)+TX, dofenapyn (1113)+TX, doramectin (alternativename) [CCN]+TX, endosulfan (294)+TX, endothion (1121)+TX, EPN (297)+TX,eprinomectin (alternative name) [CCN]+TX, ethion (309)+TX,ethoate-methyl (1134)+TX, etoxazole (320)+TX, etrimfos (1142)+TX,fenazaflor (1147)+TX, fenazaquin (328)+TX, fenbutatin oxide (330)+TX,fenothiocarb (337)+TX, fenpropathrin (342)+TX, fenpyrad (alternativename)+TX, fenpyroximate (345)+TX, fenson (1157)+TX, fentrifanil(1161)+TX, fenvalerate (349)+TX, fipronil (354)+TX, fluacrypyrim(360)+TX, fluazuron (1166)+TX, flubenzimine (1167)+TX, flucycloxuron(366)+TX, flucythrinate (367)+TX, fluenetil (1169)+TX, flufenoxuron(370)+TX, flumethrin (372)+TX, fluorbenside (1174)+TX, fluvalinate(1184)+TX, FMC 1137 (development code) (1185)+TX, formetanate (405)+TX,formetanate hydrochloride (405)+TX, formothion (1192)+TX, formparanate(1193)+TX, gamma-HCH (430)+TX, glyodin (1205)+TX, halfenprox (424)+TX,heptenophos (432)+TX, hexadecyl cyclopropanecarboxylate (IUPAC/ChemicalAbstracts name) (1216)+TX, hexythiazox (441)+TX, iodomethane (IUPACname) (542)+TX, isocarbophos (alternative name) (473)+TX, isopropylO-(methoxyaminothiophosphoryl)salicylate (IUPAC name) (473)+TX,ivermectin (alternative name) [CCN]+TX, jasmolin I (696)+TX, jasmolin II(696)+TX, jodfenphos (1248)+TX, lindane (430)+TX, lufenuron (490)+TX,malathion (492)+TX, malonoben (1254)+TX, mecarbam (502)+TX, mephosfolan(1261)+TX, mesulfen (alternative name) [CCN]+TX, methacrifos (1266)+TX,methamidophos (527)+TX, methidathion (529)+TX, methiocarb (530)+TX,methomyl (531)+TX, methyl bromide (537)+TX, metolcarb (550)+TX,mevinphos (556)+TX, mexacarbate (1290)+TX, milbemectin (557)+TX,milbemycin oxime (alternative name) [CCN]+TX, mipafox (1293)+TX,monocrotophos (561)+TX, morphothion (1300)+TX, moxidectin (alternativename) [CCN]+TX, naled (567)+TX, NC-184 (compound code)+TX, NC-512(compound code)+TX, nifluridide (1309)+TX, nikkomycins (alternativename) [CCN]+TX, nitrilacarb (1313)+TX, nitrilacarb 1:1 zinc chloridecomplex (1313)+TX, NNI-0101 (compound code)+TX, NNI-0250 (compoundcode)+TX, omethoate (594)+TX, oxamyl (602)+TX, oxydeprofos (1324)+TX,oxydisulfoton (1325)+TX, pp′-DDT (219)+TX, parathion (615)+TX,permethrin (626)+TX, petroleum oils (alternative name) (628)+TX,phenkapton (1330)+TX, phenthoate (631)+TX, phorate (636)+TX, phosalone(637)+TX, phosfolan (1338)+TX, phosmet (638)+TX, phosphamidon (639)+TX,phoxim (642)+TX, pirimiphos-methyl (652)+TX, polychloroterpenes(traditional name) (1347)+TX, polynactins (alternative name) (653)+TX,proclonol (1350)+TX, profenofos (662)+TX, promacyl (1354)+TX, propargite(671)+TX, propetamphos (673)+TX, propoxur (678)+TX, prothidathion(1360)+TX, prothoate (1362)+TX, pyrethrin 1 (696)+TX, pyrethrin II(696)+TX, pyrethrins (696)+TX, pyridaben (699)+TX, pyridaphenthion(701)+TX, pyrimidifen (706)+TX, pyrimitate (1370)+TX, quinalphos(711)+TX, quintiofos (1381)+TX, R-1492 (development code) (1382)+TX,RA-17 (development code) (1383)+TX, rotenone (722)+TX, schradan(1389)+TX, sebufos (alternative name)+TX, selamectin (alternative name)[CCN]+TX, SI-0009 (compound code)+TX, sophamide (1402)+TX, spirodiclofen(738)+TX, spiromesifen (739)+TX, SSI-121 (development code) (1404)+TX,sulfuram (alternative name) [CCN]+TX, sulfluramid (750)+TX, sulfotep(753)+TX, sulphur (754)+TX, SZI-121 (development code) (757)+TX,tau-fluvalinate (398)+TX, tebufenpyrad (763)+TX, TEPP (1417)+TX, terbam(alternative name)+TX, tetrachlorvinphos (777)+TX, tetradifon (786)+TX,tetranactin (alternative name) (653)+TX, tetrasul (1425)+TX, thiafenox(alternative name)+TX, thiocarboxime (1431)+TX, thiofanox (800)+TX,thiometon (801)+TX, thioquinox (1436)+TX, thuringiensin (alternativename) [CCN]+TX, triamiphos (1441)+TX, triarathene (1443)+TX, triazophos(820)+TX, triazuron (alternative name)+TX, trichlorfon (824)+TX,trifenofos (1455)+TX, trinactin (alternative name) (653)+TX, vamidothion(847)+TX, vaniliprole [CCN] and YI-5302 (compound code)+TX,

an algicide selected from the group of substances consisting ofbethoxazin [CCN]+TX, copper dioctanoate (IUPAC name) (170)+TX, coppersulfate (172)+TX, cybutryne [CCN]+TX, dichlone (1052)+TX, dichlorophen(232)+TX, endothal (295)+TX, fentin (347)+TX, hydrated lime [CCN]+TX,nabam (566)+TX, quinoclamine (714)+TX, quinonamid (1379)+TX, simazine(730)+TX, triphenyltin acetate (IUPAC name) (347) and triphenyltinhydroxide (IUPAC name) (347)+TX,

an anthelmintic selected from the group of substances consisting ofabamectin (1)+TX, crufomate (1011)+TX, doramectin (alternative name)[CCN]+TX, emamectin (291)+TX, emamectin benzoate (291)+TX, eprinomectin(alternative name) [CCN]+TX, ivermectin (alternative name) [CCN]+TX,milbemycin oxime (alternative name) [CCN]+TX, moxidectin (alternativename) [CCN]+TX, piperazine [CCN]+TX, selamectin (alternative name)[CCN]+TX, spinosad (737) and thiophanate (1435)+TX,

an avicide selected from the group of substances consisting ofchloralose (127)+TX, endrin (1122)+TX, fenthion (346)+TX,pyridin-4-amine (IUPAC name) (23) and strychnine (745)+TX,

a bactericide selected from the group of substances consisting of1-hydroxy-1H-pyridine-2-thione (IUPAC name) (1222)+TX,4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748)+TX,8-hydroxyquinoline sulfate (446)+TX, bronopol (97)+TX, copperdioctanoate (IUPAC name) (170)+TX, copper hydroxide (IUPAC name)(169)+TX, cresol [CCN]+TX, dichlorophen (232)+TX, dipyrithione(1105)+TX, dodicin (1112)+TX, fenaminosulf (1144)+TX, formaldehyde(404)+TX, hydrargaphen (alternative name) [CCN]+TX, kasugamycin(483)+TX, kasugamycin hydrochloride hydrate (483)+TX, nickelbis(dimethyldithiocarbamate) (IUPAC name) (1308)+TX, nitrapyrin(580)+TX, octhilinone (590)+TX, oxolinic acid (606)+TX, oxytetracycline(611)+TX, potassium hydroxyquinoline sulfate (446)+TX, probenazole(658)+TX, streptomycin (744)+TX, streptomycin sesquisulfate (744)+TX,tecloftalam (766)+TX, and thiomersal (alternative name) [CCN]+TX,

a biological agent selected from the group of substances consisting ofAdoxophyes orana GV (alternative name) (12)+TX, Agrobacteriumradiobacter (alternative name) (13)+TX, Amblyseius spp. (alternativename) (19)+TX, Anagrapha falcifera NPV (alternative name) (28)+TX,Anagrus atomus (alternative name) (29)+TX, Aphelinus abdominalis(alternative name) (33)+TX, Aphidius colemani (alternative name)(34)+TX, Aphidoletes aphidimyza (alternative name) (35)+TX, Autographacalifornica NPV (alternative name) (38)+TX, Bacillus firmus (alternativename) (48)+TX, Bacillus sphaericus Neide (scientific name) (49)+TX,Bacillus thuringiensis Berliner (scientific name) (51)+TX, Bacillusthuringiensis subsp. aizawai (scientific name) (51)+TX, Bacillusthuringiensis subsp. israelensis (scientific name) (51)+TX, Bacillusthuringiensis subsp. japonensis (scientific name) (51)+TX, Bacillusthuringiensis subsp. kurstaki (scientific name) (51)+TX, Bacillusthuringiensis subsp. tenebrionis (scientific name) (51)+TX, Beauveriabassiana (alternative name) (53)+TX, Beauveria brongniartii (alternativename) (54)+TX, Chrysoperla carnea (alternative name) (151)+TX,Cryptolaemus montrouzieri (alternative name) (178)+TX, Cydia pomonellaGV (alternative name) (191)+TX, Dacnusa sibirica (alternative name)(212)+TX, Diglyphus isaea (alternative name) (254)+TX, Encarsia formosa(scientific name) (293)+TX, Eretmocerus eremicus (alternative name)(300)+TX, Helicoverpa zea NPV (alternative name) (431)+TX,Heterorhabditis bacteriophora and H. megidis (alternative name)(433)+TX, Hippodamia convergens (alternative name) (442)+TX, Leptomastixdactylopii (alternative name) (488)+TX, Macrolophus caliginosus(alternative name) (491)+TX, Mamestra brassicae NPV (alternative name)(494)+TX, Metaphycus helvolus (alternative name) (522)+TX, Metarhiziumanisopliae var. acridum (scientific name) (523)+TX, Metarhiziumanisopliae var. anisopliae (scientific name) (523)+TX, Neodiprionsertifer NPV and N. lecontei NPV (alternative name) (575)+TX, Orius spp.(alternative name) (596)+TX, Paecilomyces fumosoroseus (alternativename) (613)+TX, Pasteuria penetrans+TX, Pasteuria thornei+TX, Pasteurianishizawae+TX, Pasteuria ramosa+TX, Phytoseiulus persimilis (alternativename) (644)+TX, Spodoptera exigua multicapsid nuclear polyhedrosis virus(scientific name) (741)+TX, Steinernema bibionis (alternative name)(742)+TX, Steinernema carpocapsae (alternative name) (742)+TX,Steinernema feltiae (alternative name) (742)+TX, Steinernema glaseri(alternative name) (742)+TX, Steinernema riobrave (alternative name)(742)+TX, Steinernema riobravis (alternative name) (742)+TX, Steinernemascapterisci (alternative name) (742)+TX, Steinernema spp. (alternativename) (742)+TX, Trichogramma spp. (alternative name) (826)+TX,Typhlodromus occidentalis (alternative name) (844) and Verticilliumlecanii (alternative name) (848)+TX,

a soil sterilant selected from the group of substances consisting ofiodomethane (IUPAC name) (542) and methyl bromide (537)+TX,

a chemosterilant selected from the group of substances consisting ofapholate [CCN]+TX, bisazir (alternative name) [CCN]+TX, busulfan(alternative name) [CCN]+TX, diflubenzuron (250)+TX, dimatif(alternative name) [CCN]+TX, hemel [CCN]+TX, hempa [CCN]+TX, metepa[CCN]+TX, methiotepa [CCN]+TX, methyl apholate [CCN]+TX, morzid[CCN]+TX, penfluoron (alternative name) [CCN]+TX, tepa [CCN]+TX,thiohempa (alternative name) [CCN]+TX, thiotepa (alternative name)[CCN]+TX, tretamine (alternative name) [CCN] and uredepa (alternativename) [CCN]+TX,

an insect pheromone selected from the group of substances consisting of(E)-dec-5-en-1-yl acetate with (E)-dec-5-en-1-ol (IUPAC name) (222)+TX,(E)-tridec-4-en-1-yl acetate (IUPAC name) (829)+TX,(E)-6-methylhept-2-en-4-ol (IUPAC name) (541)+TX,(E,Z)-tetradeca-4,10-dien-1-yl acetate (IUPAC name) (779)+TX,(Z)-dodec-7-en-1-yl acetate (IUPAC name) (285)+TX, (Z)-hexadec-11-enal(IUPAC name) (436)+TX, (Z)hexadec-11-en-1-yl acetate (IUPAC name)(437)+TX, (Z)-hexadec-13-en-11-yn-1-yl acetate (IUPAC name) (438)+TX,(Z)-icos-13-en-10-one (IUPAC name) (448)+TX, (Z)-tetradec-7-en-1-al(IUPAC name) (782)+TX, (Z)-tetradec-9-en-1-ol (IUPAC name) (783)+TX,(Z)-tetradec-9-en-1-yl acetate (IUPAC name) (784)+TX,(7E,9Z)-dodeca-7,9-dien-1-yl acetate (IUPAC name) (283)+TX,(9Z,11E)-tetradeca-9,11-dien-1-yl acetate (IUPAC name) (780)+TX,(9Z,12E)-tetradeca-9,12-dien-1-yl acetate (IUPAC name) (781)+TX,14-methyloctadec-1-ene (IUPAC name) (545)+TX, 4-methylnonan-5-ol with4-methylnonan-5-one (IUPAC name) (544)+TX, alpha-multistriatin(alternative name) [CCN]+TX, brevicomin (alternative name) [CCN]+TX,codlelure (alternative name) [CCN]+TX, codlemone (alternative name)(167)+TX, cuelure (alternative name) (179)+TX, disparlure (277)+TX,dodec-8-en-1-yl acetate (IUPAC name) (286)+TX, dodec-9-en-1-yl acetate(IUPAC name) (287)+TX, dodeca-8+ TX, 10-dien-1-yl acetate (IUPAC name)(284)+TX, dominicalure (alternative name) [CCN]+TX, ethyl4-methyloctanoate (IUPAC name) (317)+TX, eugenol (alternative name)[CCN]+TX, frontalin (alternative name) [CCN]+TX, gossyplure (alternativename) (420)+TX, grandlure (421)+TX, grandlure I (alternative name)(421)+TX, grandlure II (alternative name) (421)+TX, grandlure III(alternative name) (421)+TX, grandlure IV (alternative name) (421)+TX,hexylure [CCN]+TX, ipsdienol (alternative name) [CCN]+TX, ipsenol(alternative name) [CCN]+TX, japonilure (alternative name) (481)+TX,lineatin (alternative name) [CCN]+TX, litlure (alternative name)[CCN]+TX, looplure (alternative name) [CCN]+TX, medlure [CCN]+TX,megatomoic acid (alternative name) [CCN]+TX, methyl eugenol (alternativename) (540)+TX, muscalure (563)+TX, octadeca-2,13-dien-1-yl acetate(IUPAC name) (588)+TX, octadeca-3,13-dien-1-yl acetate (IUPAC name)(589)+TX, orfralure (alternative name) [CCN]+TX, oryctalure (alternativename) (317)+TX, ostramone (alternative name) [CCN]+TX, siglure [CCN]+TX,sordidin (alternative name) (736)+TX, sulcatol (alternative name)[CCN]+TX, tetradec-11-en-1-yl acetate (IUPAC name) (785)+TX, trimedlure(839)+TX, trimedlure A (alternative name) (839)+TX, trimedlure B₁(alternative name) (839)+TX, trimedlure B₂ (alternative name) (839)+TX,trimedlure C (alternative name) (839) and trunc-call (alternative name)[CCN]+TX,

an insect repellent selected from the group of substances consisting of2-(octylthio)ethanol (IUPAC name) (591)+TX, butopyronoxyl (933)+TX,butoxy(polypropylene glycol) (936)+TX, dibutyl adipate (IUPAC name)(1046)+TX, dibutyl phthalate (1047)+TX, dibutyl succinate (IUPAC name)(1048)+TX, diethyltoluamide [CCN]+TX, dimethyl carbate [CCN]+TX,dimethyl phthalate [CCN]+TX, ethyl hexanediol (1137)+TX, hexamide[CCN]+TX, methoquin-butyl (1276)+TX, methylneodecanamide [CCN]+TX,oxamate [CCN] and picaridin [CCN]+TX,

an insecticide selected from the group of substances consisting of1-dichloro-1-nitroethane (IUPAC/Chemical Abstracts name) (1058)+TX,1,1-dichloro-2,2-bis(4-ethylphenyl)ethane (IUPAC name) (1056), +TX,1,2-dichloropropane (IUPAC/Chemical Abstracts name) (1062)+TX,1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063)+TX,1-bromo-2-chloroethane (IUPAC/Chemical Abstracts name) (916)+TX,2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate (IUPAC name)(1451)+TX, 2,2-dichlorovinyl 2-ethylsulphinylethyl methyl phosphate(IUPAC name) (1066)+TX, 2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate(IUPAC/Chemical Abstracts name) (1109)+TX, 2-(2-butoxyethoxy)ethylthiocyanate (IUPAC/Chemical Abstracts name) (935)+TX,2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate (IUPAC/ChemicalAbstracts name) (1084)+TX, 2-(4-chloro-3,5-xylyloxy)ethanol (IUPAC name)(986)+TX, 2-chlorovinyl diethyl phosphate (IUPAC name) (984)+TX,2-imidazolidone (IUPAC name) (1225)+TX, 2-isovalerylindan-1,3-dione(IUPAC name) (1246)+TX, 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate(IUPAC name) (1284)+TX, 2-thiocyanatoethyl laurate (IUPAC name)(1433)+TX, 3-bromo-1-chloroprop-1-ene (IUPAC name) (917)+TX,3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate (IUPAC name) (1283)+TX,4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate (IUPAC name)(1285)+TX, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate (IUPACname) (1085)+TX, abamectin (1)+TX, acephate (2)+TX, acetamiprid (4)+TX,acethion (alternative name) [CCN]+TX, acetoprole [CCN]+TX, acrinathrin(9)+TX, acrylonitrile (IUPAC name) (861)+TX, alanycarb (15)+TX, aldicarb(16)+TX, aldoxycarb (863)+TX, aldrin (864)+TX, allethrin (17)+TX,allosamidin (alternative name) [CCN]+TX, allyxycarb (866)+TX,alpha-cypermethrin (202)+TX, alpha-ecdysone (alternative name) [CCN]+TX,aluminium phosphide (640)+TX, amidithion (870)+TX, amidothioate(872)+TX, aminocarb (873)+TX, amiton (875)+TX, amiton hydrogen oxalate(875)+TX, amitraz (24)+TX, anabasine (877)+TX, athidathion (883)+TX, AVI382 (compound code)+TX, AZ 60541 (compound code)+TX, azadirachtin(alternative name) (41)+TX, azamethiphos (42)+TX, azinphos-ethyl(44)+TX, azinphos-methyl (45)+TX, azothoate (889)+TX, Bacillusthuringiensis delta endotoxins (alternative name) (52)+TX, bariumhexafluorosilicate (alternative name) [CCN]+TX, barium polysulfide(IUPAC/Chemical Abstracts name) (892)+TX, barthrin [CCN]+TX, Bayer22/190 (development code) (893)+TX, Bayer 22408 (development code)(894)+TX, bendiocarb (58)+TX, benfuracarb (60)+TX, bensultap (66)+TX,beta-cyfluthrin (194)+TX, beta-cypermethrin (203)+TX, bifenthrin(76)+TX, bioallethrin (78)+TX, bioallethrin S-cyclopentenyl isomer(alternative name) (79)+TX, bioethanomethrin [CCN]+TX, biopermethrin(908)+TX, bioresmethrin (80)+TX, bis(2-chloroethyl)ether (IUPAC name)(909)+TX, bistrifluoron (83)+TX, borax (86)+TX, brofenvalerate(alternative name)+TX, bromfenvinfos (914)+TX, bromocyclen (918)+TX,bromo-DDT (alternative name) [CCN]+TX, bromophos (920)+TX,bromophos-ethyl (921)+TX, bufencarb (924)+TX, buprofezin (99)+TX,butacarb (926)+TX, butathiofos (927)+TX, butocarboxim (103)+TX, butonate(932)+TX, butoxycarboxim (104)+TX, butylpyridaben (alternative name)+TX,cadusafos (109)+TX, calcium arsenate [CCN]+TX, calcium cyanide (444)+TX,calcium polysulfide (IUPAC name) (111)+TX, camphechlor (941)+TX,carbanolate (943)+TX, carbaryl (115)+TX, carbofuran (118)+TX, carbondisulfide (IUPAC/Chemical Abstracts name) (945)+TX, carbon tetrachloride(IUPAC name) (946)+TX, carbophenothion (947)+TX, carbosulfan (119)+TX,cartap (123)+TX, cartap hydrochloride (123)+TX, cevadine (alternativename) (725)+TX, chlorbicyclen (960)+TX, chlordane (128)+TX, chlordecone(963)+TX, chlordimeform (964)+TX, chlordimeform hydrochloride (964)+TX,chlorethoxyfos (129)+TX, chlorfenapyr (130)+TX, chlorfenvinphos(131)+TX, chlorfluazuron (132)+TX, chlormephos (136)+TX, chloroform[CCN]+TX, chloropicrin (141)+TX, chlorphoxim (989)+TX, chlorprazophos(990)+TX, chlorpyrifos (145)+TX, chlorpyrifos-methyl (146)+TX,chlorthiophos (994)+TX, chromafenozide (150)+TX, cinerin I (696)+TX,cinerin II (696)+TX, cinerins (696)+TX, cis-resmethrin (alternativename)+TX, cismethrin (80)+TX, clocythrin (alternative name)+TX,cloethocarb (999)+TX, closantel (alternative name) [CCN]+TX,clothianidin (165)+TX, copper acetoarsenite [CCN]+TX, copper arsenate[CCN]+TX, copper oleate [CCN]+TX, coumaphos (174)+TX, coumithoate(1006)+TX, crotamiton (alternative name) [CCN]+TX, crotoxyphos(1010)+TX, crufomate (1011)+TX, cryolite (alternative name) (177)+TX, CS708 (development code) (1012)+TX, cyanofenphos (1019)+TX, cyanophos(184)+TX, cyanthoate (1020)+TX, cyclethrin [CCN]+TX, cycloprothrin(188)+TX, cyfluthrin (193)+TX, cyhalothrin (196)+TX, cypermethrin(201)+TX, cyphenothrin (206)+TX, cyromazine (209)+TX, cythioate(alternative name) [CCN]+TX, d-limonene (alternative name) [CCN]+TX,dtetramethrin (alternative name) (788)+TX, DAEP (1031)+TX, dazomet(216)+TX, DDT (219)+TX, decarbofuran (1034)+TX, deltamethrin (223)+TX,demephion (1037)+TX, demephion-O (1037)+TX, demephion-S (1037)+TX,demeton (1038)+TX, demeton-methyl (224)+TX, demeton-O (1038)+TX,demeton-O-methyl (224)+TX, demeton-S (1038)+TX, demeton-S-methyl(224)+TX, demeton-S-methylsulphon (1039)+TX, diafenthiuron (226)+TX,dialifos (1042)+TX, diamidafos (1044)+TX, diazinon (227)+TX, dicapthon(1050)+TX, dichlofenthion (1051)+TX, dichlorvos (236)+TX, dicliphos(alternative name)+TX, dicresyl (alternative name) [CCN]+TX, dicrotophos(243)+TX, dicyclanil (244)+TX, dieldrin (1070)+TX, diethyl5-methylpyrazol-3-yl phosphate (IUPAC name) (1076)+TX, diflubenzuron(250)+TX, dilor (alternative name) [CCN]+TX, dimefluthrin [CCN]+TX,dimefox (1081)+TX, dimetan (1085)+TX, dimethoate (262)+TX, dimethrin(1083)+TX, dimethylvinphos (265)+TX, dimetilan (1086)+TX, dinex(1089)+TX, dinex-diclexine (1089)+TX, dinoprop (1093)+TX, dinosam(1094)+TX, dinoseb (1095)+TX, dinotefuran (271)+TX, diofenolan(1099)+TX, dioxabenzofos (1100)+TX, dioxacarb (1101)+TX, dioxathion(1102)+TX, disulfoton (278)+TX, dithicrofos (1108)+TX, DNOC (282)+TX,doramectin (alternative name) [CCN]+TX, DSP (1115)+TX, ecdysterone(alternative name) [CCN]+TX, E11642 (development code) (1118)+TX,emamectin (291)+TX, emamectin benzoate (291)+TX, EMPC (1120)+TX,empenthrin (292)+TX, endosulfan (294)+TX, endothion (1121)+TX, endrin(1122)+TX, EPBP (1123)+TX, EPN (297)+TX, epofenonane (1124)+TX,eprinomectin (alternative name) [CCN]+TX, esfenvalerate (302)+TX,etaphos (alternative name) [CCN]+TX, ethiofencarb (308)+TX, ethion(309)+TX, ethiprole (310)+TX, ethoate-methyl (1134)+TX, ethoprophos(312)+TX, ethyl formate (IUPAC name) [CCN]+TX, ethyl-DDD (alternativename) (1056)+TX, ethylene dibromide (316)+TX, ethylene dichloride(chemical name) (1136)+TX, ethylene oxide [CCN]+TX, etofenprox (319)+TX,etrimfos (1142)+TX, EXD (1143)+TX, famphur (323)+TX, fenamiphos(326)+TX, fenazaflor (1147)+TX, fenchlorphos (1148)+TX, fenethacarb(1149)+TX, fenfluthrin (1150)+TX, fenitrothion (335)+TX, fenobucarb(336)+TX, fenoxacrim (1153)+TX, fenoxycarb (340)+TX, fenpirithrin(1155)+TX, fenpropathrin (342)+TX, fenpyrad (alternative name)+TX,fensulfothion (1158)+TX, fenthion (346)+TX, fenthion-ethyl [CCN]+TX,fenvalerate (349)+TX, fipronil (354)+TX, flonicamid (358)+TX,flubendiamide (CAS. Reg. No.: 272451-65-7)+TX, flucofuron (1168)+TX,flucycloxuron (366)+TX, flucythrinate (367)+TX, fluenetil (1169)+TX,flufenerim [CCN]+TX, flufenoxuron (370)+TX, flufenprox (1171)+TX,flumethrin (372)+TX, flupyradifurone+TX, fluvalinate (1184)+TX, FMC 1137(development code) (1185)+TX, fonofos (1191)+TX, formetanate (405)+TX,formetanate hydrochloride (405)+TX, formothion (1192)+TX, formparanate(1193)+TX, fosmethilan (1194)+TX, fospirate (1195)+TX, fosthiazate(408)+TX, fosthietan (1196)+TX, furathiocarb (412)+TX, furethrin(1200)+TX, gamma-cyhalothrin (197)+TX, gamma-HCH (430)+TX, guazatine(422)+TX, guazatine acetates (422)+TX, GY-81 (development code)(423)+TX, halfenprox (424)+TX, halofenozide (425)+TX, HCH (430)+TX, HEOD(1070)+TX, heptachlor (1211)+TX, heptenophos (432)+TX, heterophos[CCN]+TX, hexaflumuron (439)+TX, HHDN (864)+TX, hydramethylnon (443)+TX,hydrogen cyanide (444)+TX, hydroprene (445)+TX, hyquincarb (1223)+TX,imidacloprid (458)+TX, imiprothrin (460)+TX, indoxacarb (465)+TX,iodomethane (IUPAC name) (542)+TX, IPSP (1229)+TX, isazofos (1231)+TX,isobenzan (1232)+TX, isocarbophos (alternative name) (473)+TX, isodrin(1235)+TX, isofenphos (1236)+TX, isolane (1237)+TX, isoprocarb (472)+TX,isopropyl O-(methoxyaminothiophosphoryl)salicylate (IUPAC name)(473)+TX, isoprothiolane (474)+TX, isothioate (1244)+TX, isoxathion(480)+TX, ivermectin (alternative name) [CCN]+TX, jasmolin I (696)+TX,jasmolin II (696)+TX, jodfenphos (1248)+TX, juvenile hormone I(alternative name) [CCN]+TX, juvenile hormone II (alternative name)[CCN]+TX, juvenile hormone III (alternative name) [CCN]+TX, kelevan(1249)+TX, kinoprene (484)+TX, lambda-cyhalothrin (198)+TX, leadarsenate [CCN]+TX, lepimectin (CCN)+TX, leptophos (1250)+TX, lindane(430)+TX, lirimfos (1251)+TX, lufenuron (490)+TX, lythidathion(1253)+TX, m-cumenyl methylcarbamate (IUPAC name) (1014)+TX, magnesiumphosphide (IUPAC name) (640)+TX, malathion (492)+TX, malonoben(1254)+TX, mazidox (1255)+TX, mecarbam (502)+TX, mecarphon (1258)+TX,menazon (1260)+TX, mephosfolan (1261)+TX, mercurous chloride (513)+TX,mesulfenfos (1263)+TX, metaflumizone (CCN)+TX, metam (519)+TX,metam-potassium (alternative name) (519)+TX, metam-sodium (519)+TX,methacrifos (1266)+TX, methamidophos (527)+TX, methanesulphonyl fluoride(IUPAC/Chemical Abstracts name) (1268)+TX, methidathion (529)+TX,methiocarb (530)+TX, methocrotophos (1273)+TX, methomyl (531)+TX,methoprene (532)+TX, methoquin-butyl (1276)+TX, methothrin (alternativename) (533)+TX, methoxychlor (534)+TX, methoxyfenozide (535)+TX, methylbromide (537)+TX, methyl isothiocyanate (543)+TX, methylchloroform(alternative name) [CCN]+TX, methylene chloride [CCN]+TX, metofluthrin[CCN]+TX, metolcarb (550)+TX, metoxadiazone (1288)+TX, mevinphos(556)+TX, mexacarbate (1290)+TX, milbemectin (557)+TX, milbemycin oxime(alternative name) [CCN]+TX, mipafox (1293)+TX, mirex (1294)+TX,monocrotophos (561)+TX, morphothion (1300)+TX, moxidectin (alternativename) [CCN]+TX, naftalofos (alternative name) [CCN]+TX, naled (567)+TX,naphthalene (IUPAC/Chemical Abstracts name) (1303)+TX, NC-170(development code) (1306)+TX, NC-184 (compound code)+TX, nicotine(578)+TX, nicotine sulfate (578)+TX, nifluridide (1309)+TX, nitenpyram(579)+TX, nithiazine (1311)+TX, nitrilacarb (1313)+TX, nitrilacarb 1:1zinc chloride complex (1313)+TX, NNI-0101 (compound code)+TX, NNI-0250(compound code)+TX, nornicotine (traditional name) (1319)+TX, novaluron(585)+TX, noviflumuron (586)+TX, O-5-dichloro-4-iodophenyl O-ethylethylphosphonothioate (IUPAC name) (1057)+TX, O,O-diethylO-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate (IUPAC name)(1074)+TX, O,O-diethyl O-6-methyl-2-propylpyrimidin-4-ylphosphorothioate (IUPAC name) (1075)+TX, O,O,O′,O′-tetrapropyldithiopyrophosphate (IUPAC name) (1424)+TX, oleic acid (IUPAC name)(593)+TX, omethoate (594)+TX, oxamyl (602)+TX, oxydemetonmethyl(609)+TX, oxydeprofos (1324)+TX, oxydisulfoton (1325)+TX, pp′-DDT(219)+TX, para-dichlorobenzene [CCN]+TX, parathion (615)+TX,parathion-methyl (616)+TX, penfluoron (alternative name) [CCN]+TX,pentachlorophenol (623)+TX, pentachlorophenyl laurate (IUPAC name)(623)+TX, permethrin (626)+TX, petroleum oils (alternative name)(628)+TX, PH 60-38 (development code) (1328)+TX, phenkapton (1330)+TX,phenothrin (630)+TX, phenthoate (631)+TX, phorate (636)+TX, phosalone(637)+TX, phosfolan (1338)+TX, phosmet (638)+TX, phosnichlor (1339)+TX,phosphamidon (639)+TX, phosphine (IUPAC name) (640)+TX, phoxim (642)+TX,phoxim-methyl (1340)+TX, pirimetaphos (1344)+TX, pirimicarb (651)+TX,pirimiphos-ethyl (1345)+TX, pirimiphos-methyl (652)+TX,polychlorodicyclopentadiene isomers (IUPAC name) (1346)+TX,polychloroterpenes (traditional name) (1347)+TX, potassium arsenite[CCN]+TX, potassium thiocyanate [CCN]+TX, prallethrin (655)+TX,precocene I (alternative name) [CCN]+TX, precocene II (alternative name)[CCN]+TX, precocene III (alternative name) [CCN]+TX, primidophos(1349)+TX, profenofos (662)+TX, profluthrin [CCN]+TX, promacyl(1354)+TX, promecarb (1355)+TX, propaphos (1356)+TX, propetamphos(673)+TX, propoxur (678)+TX, prothidathion (1360)+TX, prothiofos(686)+TX, prothoate (1362)+TX, protrifenbute [CCN]+TX, pymetrozine(688)+TX, pyraclofos (689)+TX, pyrazophos (693)+TX, pyresmethrin(1367)+TX, pyrethrin I (696)+TX, pyrethrin II (696)+TX, pyrethrins(696)+TX, pyridaben (699)+TX, pyridalyl (700)+TX, pyridaphenthion(701)+TX, pyrimidifen (706)+TX, pyrimitate (1370)+TX, pyriproxyfen(708)+TX, quassia (alternative name) [CCN]+TX, quinalphos (711)+TX,quinalphos-methyl (1376)+TX, quinothion (1380)+TX, quintiofos (1381)+TX,R-1492 (development code) (1382)+TX, rafoxanide (alternative name)[CCN]+TX, resmethrin (719)+TX, rotenone (722)+TX, RU 15525 (developmentcode) (723)+TX, RU 25475 (development code) (1386)+TX, ryania(alternative name) (1387)+TX, ryanodine (traditional name) (1387)+TX,sabadilla (alternative name) (725)+TX, schradan (1389)+TX, sebufos(alternative name)+TX, selamectin (alternative name) [CCN]+TX, SI-0009(compound code)+TX, SI-0205 (compound code)+TX, SI-0404 (compoundcode)+TX, SI-0405 (compound code)+TX, silafluofen (728)+TX, SN 72129(development code) (1397)+TX, sodium arsenite [CCN]+TX, sodium cyanide(444)+TX, sodium fluoride (IUPAC/Chemical Abstracts name) (1399)+TX,sodium hexafluorosilicate (1400)+TX, sodium pentachlorophenoxide(623)+TX, sodium selenate (IUPAC name) (1401)+TX, sodium thiocyanate[CCN]+TX, sophamide (1402)+TX, spinosad (737)+TX, spiromesifen (739)+TX,spirotetrmat (CCN)+TX, sulcofuron (746)+TX, sulcofuron-sodium (746)+TX,sulfluramid (750)+TX, sulfotep (753)+TX, sulphuryl fluoride (756)+TX,sulprofos (1408)+TX, tar oils (alternative name) (758)+TX,tau-fluvalinate (398)+TX, tazimcarb (1412)+TX, TDE (1414)+TX,tebufenozide (762)+TX, tebufenpyrad (763)+TX, tebupirimfos (764)+TX,teflubenzuron (768)+TX, tefluthrin (769)+TX, temephos (770)+TX, TEPP(1417)+TX, terallethrin (1418)+TX, terbam (alternative name)+TX,terbufos (773)+TX, tetrachloroethane [CCN]+TX, tetrachlorvinphos(777)+TX, tetramethrin (787)+TX, theta-cypermethrin (204)+TX,thiacloprid (791)+TX, thiafenox (alternative name)+TX, thiamethoxam(792)+TX, thicrofos (1428)+TX, thiocarboxime (1431)+TX, thiocyclam(798)+TX, thiocyclam hydrogen oxalate (798)+TX, thiodicarb (799)+TX,thiofanox (800)+TX, thiometon (801)+TX, thionazin (1434)+TX, thiosultap(803)+TX, thiosultap-sodium (803)+TX, thuringiensin (alternative name)[CCN]+TX, tolfenpyrad (809)+TX, tralomethrin (812)+TX, transfluthrin(813)+TX, transpermethrin (1440)+TX, triamiphos (1441)+TX, triazamate(818)+TX, triazophos (820)+TX, triazuron (alternative name)+TX,trichlorfon (824)+TX, trichlormetaphos-3 (alternative name) [CCN]+TX,trichloronat (1452)+TX, trifenofos (1455)+TX, triflumuron (835)+TX,trimethacarb (840)+TX, triprene (1459)+TX, vamidothion (847)+TX,vaniliprole [CCN]+TX, veratridine (alternative name) (725)+TX, veratrine(alternative name) (725)+TX, XMC (853)+TX, xylylcarb (854)+TX, YI-5302(compound code)+TX, zeta-cypermethrin (205)+TX, zetamethrin (alternativename)+TX, zinc phosphide (640)+TX, zolaprofos (1469) and ZXI 8901(development code) (858)+TX, cyantraniliprole [736994-63-19]+TX,chlorantraniliprole [500008-45-7]+TX, cyenopyrafen [560121-52-0]+TX,cyflumetofen [400882-07-7]+TX, pyrifluquinazon [337458-27-2]+TX,spinetoram [187166-40-1+187166-15-0]+TX, spirotetramat [203313-25-1]+TX,sulfoxaflor [946578-00-3]+TX, flufiprole [704886-18-0]+TX, meperfluthrin[915288-13-0]+TX, tetramethylfluthrin [84937-88-2]+TX,

a molluscicide selected from the group of substances consisting ofbis(tributyltin) oxide (IUPAC name) (913)+TX, bromoacetamide [CCN]+TX,calcium arsenate [CCN]+TX, cloethocarb (999)+TX, copper acetoarsenite[CCN]+TX, copper sulfate (172)+TX, fentin (347)+TX, ferric phosphate(IUPAC name) (352)+TX, metaldehyde (518)+TX, methiocarb (530)+TX,niclosamide (576)+TX, niclosamide-olamine (576)+TX, pentachlorophenol(623)+TX, sodium pentachlorophenoxide (623)+TX, tazimcarb (1412)+TX,thiodicarb (799)+TX, tributyltin oxide (913)+TX, trifenmorph (1454)+TX,trimethacarb (840)+TX, triphenyltin acetate (IUPAC name) (347) andtriphenyltin hydroxide (IUPAC name) (347)+TX, pyriprole[394730-71-3]+TX,

a nematicide selected from the group of substances consisting ofAKD-3088 (compound code)+TX, 1,2-dibromo-3-chloropropane (IUPAC/ChemicalAbstracts name) (1045)+TX, 1,2-dichloropropane (IUPAC/Chemical Abstractsname) (1062)+TX, 1,2-dichloropropane with 1,3-dichloropropene (IUPACname) (1063)+TX, 1,3-dichloropropene (233)+TX,3,4-dichlorotetrahydrothiophene 1,1-dioxide (IUPAC/Chemical Abstractsname) (1065)+TX, 3-(4-chlorophenyl)-S-methylrhodanine (IUPAC name)(980)+TX, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid (IUPACname) (1286)+TX, 6-isopentenylaminopurine (alternative name) (210)+TX,abamectin (1)+TX, acetoprole [CCN]+TX, alanycarb (15)+TX, aldicarb(16)+TX, aldoxycarb (863)+TX, AZ 60541 (compound code)+TX, benclothiaz[CCN]+TX, benomyl (62)+TX, butylpyridaben (alternative name)+TX,cadusafos (109)+TX, carbofuran (118)+TX, carbon disulfide (945)+TX,carbosulfan (119)+TX, chloropicrin (141)+TX, chlorpyrifos (145)+TX,cloethocarb (999)+TX, cytokinins (alternative name) (210)+TX, dazomet(216)+TX, DBCP (1045)+TX, DCIP (218)+TX, diamidafos (1044)+TX,dichlofenthion (1051)+TX, dicliphos (alternative name)+TX, dimethoate(262)+TX, doramectin (alternative name) [CCN]+TX, emamectin (291)+TX,emamectin benzoate (291)+TX, eprinomectin (alternative name) [CCN]+TX,ethoprophos (312)+TX, ethylene dibromide (316)+TX, fenamiphos (326)+TX,fenpyrad (alternative name)+TX, fensulfothion (1158)+TX, fosthiazate(408)+TX, fosthietan (1196)+TX, furfural (alternative name) [CCN]+TX,GY-81 (development code) (423)+TX, heterophos [CCN]+TX, iodomethane(IUPAC name) (542)+TX, isamidofos (1230)+TX, isazofos (1231)+TX,ivermectin (alternative name) [CCN]+TX, kinetin (alternative name)(210)+TX, mecarphon (1258)+TX, metam (519)+TX, metam-potassium(alternative name) (519)+TX, metam-sodium (519)+TX, methyl bromide(537)+TX, methyl isothiocyanate (543)+TX, milbemycin oxime (alternativename) [CCN]+TX, moxidectin (alternative name) [CCN]+TX, Myrotheciumverrucaria composition (alternative name) (565)+TX, NC-184 (compoundcode)+TX, oxamyl (602)+TX, phorate (636)+TX, phosphamidon (639)+TX,phosphocarb [CCN]+TX, sebufos (alternative name)+TX, selamectin(alternative name) [CCN]+TX, spinosad (737)+TX, terbam (alternativename)+TX, terbufos (773)+TX, tetrachlorothiophene (IUPAC/ChemicalAbstracts name) (1422)+TX, thiafenox (alternative name)+TX, thionazin(1434)+TX, triazophos (820)+TX, triazuron (alternative name)+TX,xylenols [CCN]+TX, yl-5302 (compound code) and zeatin (alternative name)(210)+TX, fluensulfone [318290-98-1]+TX,

a nitrification inhibitor selected from the group of substancesconsisting of potassium ethylxanthate [CCN] and nitrapyrin (580)+TX,

a plant activator selected from the group of substances consisting ofacibenzolar (6)+TX, acibenzolar-S-methyl (6)+TX, probenazole (658) andReynoutria sachalinensis extract (alternative name) (720)+TX,

a rodenticide selected from the group of substances consisting of2-isovalerylindan-1,3-dione (IUPAC name) (1246)+TX,4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748)+TX,alpha-chlorohydrin [CCN]+TX, aluminium phosphide (640)+TX, antu(880)+TX, arsenous oxide (882)+TX, barium carbonate (891)+TX,bisthiosemi (912)+TX, brodifacoum (89)+TX, bromadiolone (91)+TX,bromethalin (92)+TX, calcium cyanide (444)+TX, chloralose (127)+TX,chlorophacinone (140)+TX, cholecalciferol (alternative name) (850)+TX,coumachlor (1004)+TX, coumafuryl (1005)+TX, coumatetralyl (175)+TX,crimidine (1009)+TX, difenacoum (246)+TX, difethialone (249)+TX,diphacinone (273)+TX, ergocalciferol (301)+TX, flocoumafen (357)+TX,fluoroacetamide (379)+TX, flupropadine (1183)+TX, flupropadinehydrochloride (1183)+TX, gamma-HCH (430)+TX, HCH (430)+TX, hydrogencyanide (444)+TX, iodomethane (IUPAC name) (542)+TX, lindane (430)+TX,magnesium phosphide (IUPAC name) (640)+TX, methyl bromide (537)+TX,norbormide (1318)+TX, phosacetim (1336)+TX, phosphine (IUPAC name)(640)+TX, phosphorus [CCN]+TX, pindone (1341)+TX, potassium arsenite[CCN]+TX, pyrinuron (1371)+TX, scilliroside (1390)+TX, sodium arsenite[CCN]+TX, sodium cyanide (444)+TX, sodium fluoroacetate (735)+TX,strychnine (745)+TX, thallium sulfate [CCN]+TX, warfarin (851) and zincphosphide (640)+TX,

a synergist selected from the group of substances consisting of2-(2-butoxyethoxy)ethyl piperonylate (IUPAC name) (934)+TX,5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (IUPAC name) (903)+TX,farnesol with nerolidol (alternative name) (324)+TX, MB-599 (developmentcode) (498)+TX, MGK 264 (development code) (296)+TX, piperonyl butoxide(649)+TX, piprotal (1343)+TX, propyl isomer (1358)+TX, S421 (developmentcode) (724)+TX, sesamex (1393)+TX, sesasmolin (1394) and sulfoxide(1406)+TX,

an animal repellent selected from the group of substances consisting ofanthraquinone (32)+TX, chloralose (127)+TX, copper naphthenate [CCN]+TX,copper oxychloride (171)+TX, diazinon (227)+TX, dicyclopentadiene(chemical name) (1069)+TX, guazatine (422)+TX, guazatine acetates(422)+TX, methiocarb (530)+TX, pyridin-4-amine (IUPAC name) (23)+TX,thiram (804)+TX, trimethacarb (840)+TX, zinc naphthenate [CCN] and ziram(856)+TX,

a virucide selected from the group of substances consisting of imanin(alternative name) [CCN] and ribavirin (alternative name) [CCN]+TX,

a wound protectant selected from the group of substances consisting ofmercuric oxide (512)+TX, octhilinone (590) and thiophanate-methyl(802)+TX,

and biologically active compounds selected from the group consisting ofazaconazole (60207-31-0]+TX, bitertanol [70585-36-3]+TX, bromuconazole[116255-48-2]+TX, cyproconazole [94361-06-5]+TX, difenoconazole[119446-68-3]+TX, diniconazole [83657-24-3]+TX, epoxiconazole[106325-08-0]+TX, fenbuconazole [114369-43-6]+TX, fluquinconazole[136426-54-5]+TX, flusilazole [85509-19-9]+TX, flutriafol[76674-21-0]+TX, hexaconazole [79983-71-4]+TX, imazalil [35554-44-0]+TX,imibenconazole [86598-92-7]+TX, ipconazole [125225-28-7]+TX, metconazole[125116-23-6]+TX, myclobutanil [88671-89-0]+TX, pefurazoate[101903-30-4]+TX, penconazole [66246-88-6]+TX, prothioconazole[178928-70-6]+TX, pyrifenox [88283-41-4]+TX, prochloraz [67747-09-5]+TX,propiconazole [60207-90-1]+TX, simeconazole [149508-90-7]+TX,tebuconazole [107534-96-3]+TX, tetraconazole [112281-77-3]+TX,triadimefon [43121-43-3]+TX, triadimenol [55219-65-3]+TX, triflumizole[99387-89-0]+TX, triticonazole [131983-72-7]+TX, ancymidol[12771-68-5]+TX, fenarimol [60168-88-9]+TX, nuarimol [63284-71-9]+TX,bupirimate [41483-43-6]+TX, dimethirimol [5221-53-4]+TX, ethirimol[23947-60-6]+TX, dodemorph [1593-77-7]+TX, fenpropidine [67306-00-7]+TX,fenpropimorph [67564-91-4]+TX, spiroxamine [118134-30-8]+TX, tridemorph[81412-43-3]+TX, cyprodinil [121552-61-2]+TX, mepanipyrim[110235-47-7]+TX, pyrimethanil [53112-28-0]+TX, fenpiclonil[74738-17-3]+TX, fludioxonil [131341-86-1]+TX, benalaxyl[71626-11-4]+TX, furalaxyl [57646-30-7]+TX, metalaxyl [57837-19-1]+TX,R-metalaxyl [70630-17-0]+TX, ofurace [58810-48-3]+TX, oxadixyl[77732-09-3]+TX, benomyl [17804-35-2]+TX, carbendazim [10605-21-7]+TX,debacarb [62732-91-6]+TX, fuberidazole [3878-19-1]+TX, thiabendazole[148-79-8]+TX, chlozolinate [84332-86-5]+TX, dichlozoline[24201-58-9]+TX, iprodione [36734-19-7]+TX, myclozoline [54864-61-8]+TX,procymidone [32809-16-8]+TX, vinclozoline [50471-44-8]+TX, boscalid[188425-85-6]+TX, carboxin [5234-68-4]+TX, fenfuram [24691-80-3]+TX,flutolanil [66332-96-5]+TX, mepronil [55814-41-0]+TX, oxycarboxin[5259-88-1]+TX, penthiopyrad [183675-82-3]+TX, thifluzamide[130000-40-7]+TX, guazatine [108173-90-6]+TX, dodine [2439-10-3][112-65-2] (free base)+TX, iminoctadine [13516-27-3]+TX, azoxystrobin[131860-33-8]+TX, dimoxystrobin [149961-52-4]+TX, enestroburin {Proc.BCPC, Int. Congr., Glasgow, 2003, 1, 93}+TX, fluoxastrobin[361377-29-9]+TX, kresoxim-methyl [143390-89-0]+TX, metominostrobin[133408-50-1]+TX, trifloxystrobin [141517-21-7]+TX, orysastrobin[248593-16-0]+TX, picoxystrobin [117428-22-5]+TX, pyraclostrobin[175013-18-0]+TX, ferbam [14484-64-1]+TX, mancozeb [8018-01-7]+TX, maneb[12427-38-2]+TX, metiram [9006-42-2]+TX, propineb [12071-83-9]+TX,thiram [137-26-8]+TX, zineb [12122-67-7]+TX, ziram [137-30-4]+TX,captafol [2425-06-1]+TX, captan [133-06-2]+TX, dichlofluanid[1085-98-9]+TX, fluoroimide [41205-21-4]+TX, folpet [133-07-3]+TX,tolylfluanid [731-27-1]+TX, bordeaux mixture [8011-63-0]+TX,copperhydroxid [20427-59-2]+TX, copperoxychlorid [1332-40-7]+TX,coppersulfat [7758-98-7]+TX, copperoxid [1317-39-1]+TX, mancopper[53988-93-5]+TX, oxine-copper [10380-28-6]+TX, dinocap [131-72-6]+TX,nitrothal-isopropyl [10552-74-6]+TX, edifenphos [17109-49-8]+TX,iprobenphos [26087-47-8]+TX, isoprothiolane [50512-35-1]+TX, phosdiphen[36519-00-3]+TX, pyrazophos [13457-18-6]+TX, tolclofos-methyl[57018-04-9]+TX, acibenzolar-S-methyl [135158-54-2]+TX, anilazine[101-05-3]+TX, benthiavalicarb [413615-35-7]+TX, blasticidin-S[2079-00-7]+TX, chinomethionat [2439-01-2]+TX, chloroneb [2675-77-6]+TX,chlorothalonil [1897-45-6]+TX, cyflufenamid [180409-60-3]+TX, cymoxanil[57966-95-7]+TX, dichlone [117-80-6]+TX, diclocymet [139920-32-4]+TX,diclomezine [62865-36-5]+TX, dicloran [99-30-9]+TX, diethofencarb[87130-20-9]+TX, dimethomorph [110488-70-5]+TX, SYP-L190 (Flumorph)[211867-47-9]+TX, dithianon [3347-22-6]+TX, ethaboxam [162650-77-3]+TX,etridiazole [2593-15-9]+TX, famoxadone [131807-57-3]+TX, fenamidone[161326-34-7]+TX, fenoxanil [115852-48-7]+TX, fentin [668-34-8]+TX,ferimzone [89269-64-7]+TX, fluazinam [79622-59-6]+TX, fluopicolide[239110-15-7]+TX, flusulfamide [106917-52-6]+TX, fenhexamid[126833-17-8]+TX, fosetyl-aluminium [39148-24-8]+TX, hymexazol[10004-44-1]+TX, iprovalicarb [140923-17-7]+TX, IKF-916 (Cyazofamid)[120116-88-3]+TX, kasugamycin [6980-18-3]+TX, methasulfocarb[66952-49-6]+TX, metrafenone [220899-03-6]+TX, pencycuron[66063-05-6]+TX, phthalide [27355-22-2]+TX, polyoxins [11113-80-7]+TX,probenazole [27605-76-1]+TX, propamocarb [25606-41-1]+TX, proquinazid[189278-12-4]+TX, pyroquilon [57369-32-1]+TX, quinoxyfen[124495-18-7]+TX, quintozene [82-68-8]+TX, sulphur [7704-34-9]+TX,tiadinil [223580-51-6]+TX, triazoxide [72459-58-6]+TX, tricyclazole[41814-78-2]+TX, triforine [26644-46-2]+TX, validamycin [37248-47-8]+TX,zoxamide (RH7281) [156052-68-5]+TX, mandipropamid [374726-62-2]+TX,isopyrazam [881685-58-1]+TX, sedaxane [874967-67-6]+TX,3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid(9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl)-amide(disclosed in WO 2007/048556)+TX,3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid[2-(2,4-dichlorophenyl)-2-methoxy-1-methyl-ethyl]-amide (disclosed in WO2008/148570)+TX,1-[4-[4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone+TX,1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone[1003318-67-9], both disclosed in WO 2010/123791, WO 2008/013925, WO2008/013622 and WO 2011/051243 page 20)+TX, and3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid(3′,4′,5′-trifluorobiphenyl-2-yl)-amide (disclosed in WO2006/087343)+TX.

The references in square brackets behind the active ingredients, e.g.[3878-19-1] refer to the Chemical Abstracts Registry number. The abovedescribed mixing partners are known. Where the active ingredients areincluded in “The Pesticide Manual” [The Pesticide Manual—A WorldCompendium; Thirteenth Edition; Editor: C. D. S. Tomlin; The BritishCrop Protection Council], they are described therein under the entrynumber given in round brackets hereinabove for the particular compound;for example, the compound “abamectin” is described under entry number(1). Where “[CCN]” is added hereinabove to the particular compound, thecompound in question is included in the “Compendium of Pesticide CommonNames”, which is accessible on the internet [A. Wood; Compendium ofPesticide Common Names, Copyright © 1995-2004]; for example, thecompound “acetoprole” is described under the internet address:http://www.alanwood.net/pesticides/acetoprole.html.

Most of the active ingredients described above are referred tohereinabove by a so-called “common name”, the relevant “ISO common name”or another “common name” being used in individual cases. If thedesignation is not a “common name”, the nature of the designation usedinstead is given in round brackets for the particular compound; in thatcase, the IUPAC name, the IUPAC/Chemical Abstracts name, a “chemicalname”, a “traditional name”, a “compound name” or a “development code”is used or, if neither one of those designations nor a “common name” isused, an “alternative name” is employed. “CAS Reg. No” means theChemical Abstracts Registry Number.

The mass ratio of any two ingredients in each combination is selected asto give the desired, for example, synergistic action. In general, themass ratio would vary depending on the specific ingredient and how manyingredients are present in the combination. Generally, the mass ratiobetween any two ingredients in any combination of the present invention,independently of one another, is from 100:1 to 1:100, including from99:1, 98:2, 97:3, 96:4, 95:5, 94:6, 93:7, 92:8, 91:9, 90:10, 89:11,88:12, 87:13, 86:14, 85:15, 84:16, 83:17, 82:18, 81:19, 80:20, 79:21,78:22, 77:23, 76:24, 75:25, 74:26, 73:27, 72:28, 71:29, 70:30, 69:31,68:32, 67:33, 66:34, 65:45, 64:46, 63:47, 62:48, 61:49, 60:40, 59:41,58:42, 57:43, 56:44, 55:45, 54:46, 53:47, 52:48, 51:49, 50:50, 49:51,48:52, 47:53, 46:54, 45:55, 44:56, 43:57, 42:58, 41:59, 40:60, 39:61,38:62, 37:63, 36:64, 35:65, 34:66, 33:67, 32:68, 31:69, 30:70, 29:71,28:72, 27:73, 26:74, 25:75, 24:76, 23:77, 22:78, 21:79, 20:80, 19:81,18:82, 17:83, 16:84, 15:85, 14:86, 13:87, 12:88, 11:89, 10:90, 9:91,8:92, 7:93, 6:94, 5:95, 4:96, 3:97, 2:98, to 1:99. Preferred mass ratiosbetween any two components of present invention are from 75:1 to 1:75,more preferably, 50:1 to 1.50, especially 25:1 to 1:25, advantageously10:1 to 1:10, such as 5:1 to 1:5, for example 1:3 to 3:1. The mixingratios are understood to include, on the one hand, ratios by mass andalso, on other hand, molar ratios.

Examples of application methods for the compounds of the invention andcompositions thereof, that is the methods of controlling pests/fungi inthe agriculture, are spraying, atomizing, dusting, brushing on,dressing, scattering or pouring—which are to be selected to suit theintended aims of the prevailing circumstances.

A preferred method of application in agriculture is application to thefoliage of the plants (foliar application), it being possible to selectfrequency and rate of application to match the danger of infestationwith the pest/fungi in question. Alternatively, the active ingredientcan reach the plants via the root system (systemic action), by applyingthe compound to the locus of the plants, for example by application of aliquid composition of the compound into the soil (by drenching), or byapplying a solid form of the compound in the form of granules to thesoil (soil application). In the case of paddy rice plants, such granulescan be metered into the flooded paddy-field.

Typical rates of application per hectare is generally 1 to 2000 g ofactive ingredient per hectare, in particular 10 to 1000 g/ha, preferably10 to 600 g/ha, such as 50 to 300 g/ha.

The compounds of the invention and compositions thereof are alsosuitable for the protection of plant propagation material, for exampleseeds, such as fruit, tubers or kernels, or nursery plants, againstpests of the abovementioned type. The propagation material can betreated with the compound prior to planting, for example seed can betreated prior to sowing. Alternatively, the compound can be applied toseed kernels (coating), either by soaking the kernels in a liquidcomposition or by applying a layer of a solid composition. It is alsopossible to apply the compositions when the propagation material isplanted to the site of application, for example into the seed furrowduring drilling. These treatment methods for plant propagation materialand the plant propagation material thus treated are further subjects ofthe invention. Typical treatment rates would depend on the plant andpest/fungi to be controlled and are generally between 1 to 200 grams per100 kg of seeds, preferably between 5 to 150 grams per 100 kg of seeds,such as between 10 to 100 grams per 100 kg of seeds.

The term seed embraces seeds and plant propagules of all kinds includingbut not limited to true seeds, seed pieces, suckers, corns, bulbs,fruit, tubers, grains, rhizomes, cuttings, cut shoots and the like andmeans in a preferred embodiment true seeds.

The present invention also comprises seeds coated or treated with orcontaining a compound of formula I. The term “coated or treated withand/or containing” generally signifies that the active ingredient is forthe most part on the surface of the seed at the time of application,although a greater or lesser part of the ingredient may penetrate intothe seed material, depending on the method of application. When the saidseed product is (re)planted, it may absorb the active ingredient. In anembodiment, the present invention makes available a plant propagationmaterial adhered thereto with a compound of formula (I). Further, it ishereby made available, a composition comprising a plant propagationmaterial treated with a compound of formula (I).

Seed treatment comprises all suitable seed treatment techniques known inthe art, such as seed dressing, seed coating, seed dusting, seed soakingand seed pelleting. The seed treatment application of the compoundformula I can be carried out by any known methods, such as spraying orby dusting the seeds before sowing or during the sowing/planting of theseeds.

Suitable target plants are, in particular, cereals, such as wheat,barley, rye, oats, rice, maize or sorghum; beet, such as sugar or fodderbeet; fruit, for example pomaceous fruit, stone fruit or soft fruit,such as apples, pears, plums, peaches, almonds, cherries or berries, forexample strawberries, raspberries or blackberries; leguminous plants,such as beans, lentils, peas or soya; oil plants, such as oilseed rape,mustard, poppies, olives, sunflowers, coconut, castor, cocoa or groundnuts; cucurbits, such as pumpkins, cucumbers or melons; fibre plants,such as cotton, flax, hemp or jute; citrus fruit, such as oranges,lemons, grapefruit or tangerines; vegetables, such as spinach, lettuce,asparagus, cabbages, carrots, onions, tomatoes, potatoes or bellpeppers; Lauraceae, such as avocado, Cinnamonium or camphor; and alsotobacco, nuts, coffee, eggplants, sugarcane, tea, pepper, grapevines,hops, the plantain family, latex plants and ornamentals (such asflowers, amd lawn grass or turf).

In an embodiment, the plant is selected from cereals, corn, soybean,rice, sugarcane, vegetables and oil plants.

The term “plant” is to be understood as including also plants which havebeen so transformed by the use of recombinant DNA techniques that theyare capable of synthesising one or more selectively acting toxins, suchas are known, for example, from toxin-producing bacteria, especiallythose of the genus Bacillus.

Toxins that can be expressed by such transgenic plants include, forexample, insecticidal proteins from Bacillus cereus or Bacilluspopilliae; or insecticidal proteins from Bacillus thuringiensis, such asδ-endotoxins, e.g. Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A,Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g. Vip1,Vip2, Vip3 or Vip3A; or insecticidal proteins of bacteria colonisingnematodes, for example Photorhabdus spp. or Xenorhabdus spp., such asPhotorhabdus luminescens, Xenorhabdus nematophilus; toxins produced byanimals, such as scorpion toxins, arachnid toxins, wasp toxins and otherinsect-specific neurotoxins; toxins produced by fungi, such asStreptomycetes toxins, plant lectins, such as pea lectins, barleylectins or snowdrop lectins; agglutinins; proteinase inhibitors, such astrypsin inhibitors, serine protease inhibitors, patatin, cystatin,papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin,maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolismenzymes, such as 3-hydroxysteroidoxidase,ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidases, ecdysoneinhibitors, HMG-COA-reductase, ion channel blockers, such as blockers ofsodium or calcium channels, juvenile hormone esterase, diuretic hormonereceptors, stilbene synthase, bibenzyl synthase, chitinases andglucanases.

In the context of the present invention there are to be understood byδ-endotoxins, for example Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A,Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for exampleVip1, Vip2, Vip3 or Vip3A, expressly also hybrid toxins, truncatedtoxins and modified toxins. Hybrid toxins are produced recombinantly bya new combination of different domains of those proteins (see, forexample, WO 02/15701). Truncated toxins, for example a truncated Cry1Ab,are known. In the case of modified toxins, one or more amino acids ofthe naturally occurring toxin are replaced. In such amino acidreplacements, preferably non-naturally present protease recognitionsequences are inserted into the toxin, such as, for example, in the caseof Cry3A055, a cathepsin-G-recognition sequence is inserted into a Cry3Atoxin (see WO 03/018810).

Examples of such toxins or transgenic plants capable of synthesisingsuch toxins are disclosed, for example, in EP-A-0 374 753, WO 93/07278,WO 95/34656, EP-A-0 427 529, EP-A-451 878 and WO 03/052073.

The processes for the preparation of such transgenic plants aregenerally known to the person skilled in the art and are described, forexample, in the publications mentioned above. Cryl-type deoxyribonucleicacids and their preparation are known, for example, from WO 95/34656,EP-A-0 367 474, EP-A-0 401 979 and WO 90/13651.

The toxin contained in the transgenic plants imparts to the plantstolerance to harmful insects. Such insects can occur in any taxonomicgroup of insects, but are especially commonly found in the beetles(Coleoptera), two-winged insects (Diptera) and butterflies(Lepidoptera).

Transgenic plants containing one or more genes that code for aninsecticidal resistance and express one or more toxins are known andsome of them are commercially available. Examples of such plants are:YieldGard® (maize variety that expresses a Cry1Ab toxin); YieldGardRootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGardPlus® (maize variety that expresses a Cry1Ab and a Cry3Bb1 toxin);Starlink® (maize variety that expresses a Cry9C toxin); Herculex I®(maize variety that expresses a Cry1Fa2 toxin and the enzymephosphinothricine N-acetyltransferase (PAT) to achieve tolerance to theherbicide glufosinate ammonium); NuCOTN 33B® (cotton variety thatexpresses a Cry1Ac toxin); Bollgard I® (cotton variety that expresses aCry1Ac toxin); Bollgard II® (cotton variety that expresses a Cry1Ac anda Cry2Ab toxin); VipCot® (cotton variety that expresses a Vip3A and aCry1Ab toxin); NewLeaf® (potato variety that expresses a Cry3A toxin);NatureGard®, Agrisure® GT Advantage (GA21 glyphosate-tolerant trait),Agrisure® CB Advantage (Bt11 corn borer (CB) trait) and Protecta®.

Further examples of such transgenic plants are:

1. Bt11 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790St. Sauveur, France, registration number C/FR/96/05/10. Geneticallymodified Zea mays which has been rendered resistant to attack by theEuropean corn borer (Ostrinia nubilalis and Sesamia nonagrioides) bytransgenic expression of a truncated Cry1Ab toxin. Bt11 maize alsotransgenically expresses the enzyme PAT to achieve tolerance to theherbicide glufosinate ammonium.2. Bt176 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790St. Sauveur, France, registration number C/FR/96/05/10. Geneticallymodified Zea mays which has been rendered resistant to attack by theEuropean corn borer (Ostrinia nubilalis and Sesamia nonagrioides) bytransgenic expression of a Cry1Ab toxin. Bt176 maize also transgenicallyexpresses the enzyme PAT to achieve tolerance to the herbicideglufosinate ammonium.3. MIR604 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790St. Sauveur, France, registration number C/FR/96/05/10. Maize which hasbeen rendered insect-resistant by transgenic expression of a modifiedCry3A toxin. This toxin is Cry3A055 modified by insertion of acathepsin-G-protease recognition sequence. The preparation of suchtransgenic maize plants is described in WO 03/018810.4. MON 863 Maize from Monsanto Europe S. A. 270-272 Avenue de Tervuren,B-1150 Brussels, Belgium, registration number C/DE/02/9. MON 863expresses a Cry3Bb1 toxin and has resistance to certain Coleopterainsects.5. IPC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de Tervuren,B-1150 Brussels, Belgium, registration number C/ES/96/02.6. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7B-1160 Brussels, Belgium, registration number C/NL/00/10. Geneticallymodified maize for the expression of the protein Cry1F for achievingresistance to certain Lepidoptera insects and of the PAT protein forachieving tolerance to the herbicide glufosinate ammonium.7. NK603×MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue deTervuren, B-1150 Brussels, Belgium, registration number C/GB/02/M3/03.Consists of conventionally bred hybrid maize varieties by crossing thegenetically modified varieties NK603 and MON 810. NK603×MON 810 Maizetransgenically expresses the protein CP4 EPSPS, obtained fromAgrobacterium sp. strain CP4, which imparts tolerance to the herbicideRoundup® (contains glyphosate), and also a Cry1Ab toxin obtained fromBacillus thuringiensis subsp. kurstaki which brings about tolerance tocertain Lepidoptera, include the European corn borer.

Generally, a compound of the present invention is used in the form of acomposition (e.g. formulation) containing a carrier. A compound of theinvention and compositions thereof can be used in various forms such asaerosol dispenser, capsule suspension, cold fogging concentrate,dustable powder, emulsifiable concentrate, emulsion oil in water,emulsion water in oil, encapsulated granule, fine granule, flowableconcentrate for seed treatment, gas (under pressure), gas generatingproduct, granule, hot fogging concentrate, macrogranule, microgranule,oil dispersible powder, oil miscible flowable concentrate, oil miscibleliquid, paste, plant rodlet, powder for dry seed treatment, seed coatedwith a pesticide, soluble concentrate, soluble powder, solution for seedtreatment, suspension concentrate (flowable concentrate), ultra lowvolume (ulv) liquid, ultra low volume (ulv) suspension, waterdispersible granules or tablets, water dispersible powder for slurrytreatment, water soluble granules or tablets, water soluble powder forseed treatment and wettable powder.

A formulation typically comprises a liquid or solid carrier andoptionally one or more customary formulation auxiliaries, which may besolid or liquid auxiliaries, for example unepoxidized or epoxidizedvegetable oils (for example epoxidized coconut oil, rapeseed oil or soyaoil), antifoams, for example silicone oil, preservatives, clays,inorganic compounds, viscosity regulators, surfactant, binders and/ortackifiers. The composition may also further comprise a fertilizer, amicronutrient donor or other preparations which influence the growth ofplants as well as comprising a combination containing the compound ofthe invention with one or more other biologically active agents, such asbactericides, fungicides, nematocides, plant activators, acaricides, andinsecticides.

Accordingly, the present invention also makes available a compositioncomprising a compound of the invention and an agronomicaly carrier andoptionally one or more customary formulation auxiliaries.

The compositions are prepared in a manner known per se, in the absenceof auxiliaries for example by grinding, screening and/or compressing asolid compound of the present invention and in the presence of at leastone auxiliary for example by intimately mixing and/or grinding thecompound of the present invention with the auxiliary (auxiliaries). Inthe case of solid compounds of the invention, the grinding/milling ofthe compounds is to ensure specific particle size. These processes forthe preparation of the compositions and the use of the compounds of theinvention for the preparation of these compositions are also a subjectof the invention.

Examples of compositions for use in agriculture are emulsifiableconcentrates, suspension concentrates, microemulsions, oil dispersibles,directly sprayable or dilutable solutions, spreadable pastes, diluteemulsions, soluble powders, dispersible powders, wettable powders,dusts, granules or encapsulations in polymeric substances, whichcomprise—at least—a compound according to the invention and the type ofcomposition is to be selected to suit the intended aims and theprevailing circumstances.

Examples of suitable liquid carriers are unhydrogenated or partiallyhydrogenated aromatic hydrocarbons, preferably the fractions C₈ to C₁₂of alkylbenzenes, such as xylene mixtures, alkylated naphthalenes ortetrahydronaphthalene, aliphatic or cycloaliphatic hydrocarbons, such asparaffins or cyclohexane, alcohols such as ethanol, propanol or butanol,glycols and their ethers and esters such as propylene glycol,dipropylene glycol ether, ethylene glycol or ethylene glycol monomethylether or ethylene glycol monoethyl ether, ketones, such ascyclohexanone, isophorone or diacetone alcohol, strongly polar solvents,such as N-methylpyrrolid-2-one, dimethyl sulfoxide orN,N-dimethylformamide, water, unepoxidized or epoxidized vegetable oils,such as unexpodized or epoxidized rapeseed, castor, coconut or soya oil,and silicone oils.

Examples of solid carriers which are used for example for dusts anddispersible powders are, as a rule, ground natural minerals such ascalcite, talc, kaolin, montmorillonite or attapulgite. To improve thephysical properties, it is also possible to add highly disperse silicasor highly disperse absorptive polymers. Suitable particulate adsorptivecarriers for granules are porous types, such as pumice, brick grit,sepiolite or bentonite, and suitable non-sorptive carrier materials arecalcite or sand. In addition, a large number of granulated materials ofinorganic or organic nature can be used, in particular dolomite orcomminuted plant residues.

Suitable surface-active compounds are, depending on the type of theactive ingredient to be formulated, non-ionic, cationic and/or anionicsurfactants or surfactant mixtures which have good emulsifying,dispersing and wetting properties. The surfactants mentioned below areonly to be considered as examples; a large number of further surfactantswhich are conventionally used in the art of formulation and suitableaccording to the invention are described in the relevant literature.

Suitable non-ionic surfactants are, especially, polyglycol etherderivatives of aliphatic or cycloaliphatic alcohols, of saturated orunsaturated fatty acids or of alkyl phenols which may containapproximately 3 to approximately 30 glycol ether groups andapproximately 8 to approximately 20 carbon atoms in the (cyclo)aliphatichydrocarbon radical or approximately 6 to approximately 18 carbon atomsin the alkyl moiety of the alkyl phenols. Also suitable arewater-soluble polyethylene oxide adducts with polypropylene glycol,ethylenediaminopolypropylene glycol or alkyl polypropylene glycol having1 to approximately 10 carbon atoms in the alkyl chain and approximately20 to approximately 250 ethylene glycol ether groups and approximately10 to approximately 100 propylene glycol ether groups. Normally, theabovementioned compounds contain 1 to approximately 5 ethylene glycolunits per propylene glycol unit. Examples which may be mentioned arenonylphenoxypolyethoxyethanol, castor oil polyglycol ether,polypropylene glycol/polyethylene oxide adducts,tributylphenoxypolyethoxyethanol, polyethylene glycol oroctylphenoxypolyethoxyethanol. Also suitable are fatty acid esters ofpolyoxyethylene sorbitan, such as polyoxyethylene sorbitan trioleate.

The cationic surfactants are, especially, quarternary ammonium saltswhich generally have at least one alkyl radical of approximately 8 toapproximately 22 C atoms as substituents and as further substituents(unhalogenated or halogenated) lower alkyl or hydroxyalkyl or benzylradicals. The salts are preferably in the form of halides,methylsulfates or ethylsulfates. Examples are stearyltrimethylammoniumchloride and benzylbis(2-chloroethyl)ethylammonium bromide.

Examples of suitable anionic surfactants are water-soluble soaps orwater-soluble synthetic surface-active compounds. Examples of suitablesoaps are the alkali, alkaline earth or (unsubstituted or substituted)ammonium salts of fatty acids having approximately 10 to approximately22 C atoms, such as the sodium or potassium salts of oleic or stearicacid, or of natural fatty acid mixtures which are obtainable for examplefrom coconut or tall oil; mention must also be made of the fatty acidmethyl taurates. However, synthetic surfactants are used morefrequently, in particular fatty sulfonates, fatty sulfates, sulfonatedbenzimidazole derivatives or alkylaryl sulfonates. As a rule, the fattysulfonates and fatty sulfates are present as alkali, alkaline earth or(substituted or unsubstituted) ammonium salts and they generally have analkyl radical of approximately 8 to approximately 22 C atoms, alkyl alsoto be understood as including the alkyl moiety of acyl radicals;examples which may be mentioned are the sodium or calcium salts oflignosulfonic acid, of the dodecylsulphuric ester or of a fatty alcoholsulfate mixture prepared from natural fatty acids. This group alsoincludes the salts of the sulphuric esters and sulfonic acids of fattyalcohol/ethylene oxide adducts. The sulfonated benzimidazole derivativespreferably contain 2 sulphonyl groups and a fatty acid radical ofapproximately 8 to approximately 22 C atoms. Examples ofalkylarylsulfonates are the sodium, calcium or triethanolammonium saltsof decylbenzenesulfonic acid, of dibutylnaphthalenesulfonic acid or of anaphthalenesulfonic acid/formaldehyde condensate. Also possible are,furthermore, suitable phosphates, such as salts of the phosphoric esterof a p-nonylphenol/(4-14)ethylene oxide adduct, or phospholipids.

As a rule, the compositions comprise 0.1 to 99%, especially 0.1 to 95%,of compound according to the present invention and 1 to 99.9%,especially 5 to 99.9%, of at least one solid or liquid carrier, it beingpossible as a rule for 0 to 25%, especially 0.1 to 20%, of thecomposition to be surfactants (% in each case meaning percent byweight). Whereas concentrated compositions tend to be preferred forcommercial goods, the end consumer as a rule uses dilute compositionswhich have substantially lower concentrations of active ingredient.Preferred compositions are composed in particular as follows (%=percentby weight):

Emulsifiable Concentrates:

active ingredient: 1 to 95%, preferably 5 to 20%

surfactant: 1 to 30%, preferably 10 to 20%

solvent: 5 to 98%, preferably 70 to 85%

Dusts:

active ingredient: 0.1 to 10%, preferably 0.1 to 1%

solid carrier: 99.9 to 90%, preferably 99.9 to 99%

Suspension Concentrates and Flowable Concentrates:

active ingredient: 5 to 75%, preferably 10 to 50%

water: 94 to 24%, preferably 88 to 30%

surfactant: 1 to 40%, preferably 2 to 30%

Wettable Powders:

active ingredient: 0.5 to 90%, preferably 1 to 80%

surfactant: 0.5 to 20%, preferably 1 to 15%

solid carrier: 5 to 99%, preferably 15 to 98%

Granulates:

active ingredient: 0.5 to 30%, preferably 3 to 15%

solid carrier: 99.5 to 70%, preferably 97 to 85%

FORMULATION EXAMPLES %=Percent by Weight Example F1 EmulsionConcentrates

a) b) c) Active ingredient 25% 40% 50% Calcium dodecylbenzenesulfonate 5%  8%  6% Castor oil polyethylene  5% — — glycol ether (36 mol of EO)Tributylphenoxypolyethylene glycol — 12%  4% ether (30 mol of EO)Cyclohexanone — 15% 20% Xylene mixture 65% 25% 20%Emulsions of any desired concentration can be prepared from suchconcentrates by dilution with water.

Example F2 Solutions

a) b) c) d) Active ingredient 80% 10% 5% 95% Ethylene glycol monomethyl20% — — — ether Polyethylene glycol — 70% — — MW 400N-Methylpyrrolid-2-one — 20% — — Epoxidized coconut oil — — 1%  5%Petroleum ether — — 94%  — (boiling range: 160-190°)The solutions are suitable for use in the form of microdrops.

Example F3 Granules

a) b) c) d) Active ingredient 5% 10% 8% 21% Kaolin 94% — 79% 54% Highlydisperse silica 1% — 13% 7% Attapulgite — 90% — 18%The active ingredient is dissolved in dichloromethane, the solution issprayed onto the carrier(s), and the solvent is subsequently evaporatedin vacuo.

Example F4 Dusts

a) b) Active ingredient 2% 5% Highly disperse silica 1% 5% Talc 97%  —Kaolin — 90% Ready-to-use dusts are obtained by intimately mixing the carriers andthe active ingredient.

Example F5 Wettable Powders

a) b) c) Active ingredient 25% 50% 75% Sodium lignosulfonate 5% 5% —Sodium lauryl sulfate 3% — 5% Sodium diisobutyl- — 6% 10%naphthalenesulfonate Octylphenoxypolyethylene glycol — 2% — ether (7-8mol of EO) Highly disperse silica 5% 10% 10% Kaolin 62% 27% —The active ingredient is mixed with the additives and the mixture isground thoroughly in a suitable mill. This gives wettable powders, whichcan be diluted with water to give suspensions of any desiredconcentration.

Example F6 Extruder Granules

Active ingredient 10% Sodium lignosulfonate 2% Carboxymethylcellulose 1%Kaolin 87%The active ingredient is mixed with the additives, and the mixture isground, moistened with water, extruded, granulated and dried in a streamof air.

Example F7 Coated Granules

Active ingredient 3% Polyethylene glycol (MW 200) 3% Kaolin 94%In a mixer, the finely ground active ingredient is applied uniformly tothe kaolin, which has been moistened with the polyethylene glycol. Thisgives dust-free coated granules.

Example F8 Suspension Concentrate

Active ingredient 40% Ethylene glycol 10% Nonylphenoxypolyethyleneglycol ether (15 mol of EO)  6% Sodium lignosulfonate 10%Carboxymethylcellulose  1% 37% aqueous formaldehyde solution 0.2% Silicone oil (75% aqueous emulsion) 0.8%  Water 32%The finely ground active ingredient is mixed intimately with theadditives. Suspensions of any desired concentration can be prepared fromthe thus resulting suspension concentrate by dilution with water.

Example F9 Powders for Dry Seed Treatment

a) b) c) active ingredient 25% 50% 75% light mineral oil 5% 5%  5%highly dispersed silicic acid 5% 5% — Kaolin 65% 40% — Talcum — — 20%The combination is thoroughly mixed with the adjuvants and the mixtureis thoroughly ground in a suitable mill, affording powders that can beused directly for seed treatment.

Example F10 Emulsifiable Concentrate

active ingredient 10% octylphenol polyethylene glycol ether 3% (4-5 molof ethylene oxide) calcium dodecylbenzenesulfonate 3% castor oilpolyglycol ether (35 mol of ethylene oxide) 4% Cyclohexanone 30% xylenemixture 50%Emulsions of any required dilution, which can be used in plantprotection, can be obtained from this concentrate by dilution withwater.

Example F11 Flowable Concentrate for Seed Treatment

active ingredients 40%  propylene glycol 5% copolymer butanol PO/EO 2%Tristyrenephenole with 10-20 moles EO 2% 1,2-benzisothiazolin-3-one (inthe form of a 20% solution 0.5%   in water) monoazo-pigment calcium salt5% Silicone oil (in the form of a 75% emulsion in water) 0.2%   Water45.3%  

The finely ground combination is intimately mixed with the adjuvants,giving a suspension concentrate from which suspensions of any desireddilution can be obtained by dilution with water. Using such dilutions,living plants as well as plant propagation material can be treated andprotected against infestation by microorganisms, by spraying, pouring orimmersion.

Examples of foliar formulation types for pre-mix compositions are:

-   -   GR: Granules    -   WP: wettable powders    -   WG: water dispersable granules (powders)    -   SG: water soluble granules    -   SL: soluble concentrates    -   EC: emulsifiable concentrate    -   EW: emulsions, oil in water    -   ME: micro-emulsion    -   SC: aqueous suspension concentrate    -   CS: aqueous capsule suspension    -   OD: oil-based suspension concentrate, and    -   SE: aqueous suspo-emulsion.

Whereas, examples of seed treatment formulation types for pre-mixcompositions are:

-   -   WS: wettable powders for seed treatment slurry    -   LS: solution for seed treatment    -   ES: emulsions for seed treatment    -   FS: suspension concentrate for seed treatment    -   WG: water dispersible granules, and    -   CS: aqueous capsule suspension.

Examples of formulation types suitable for tank-mix compositions aresolutions, dilute emulsions, suspensions, or a mixture thereof, anddusts.

As with the nature of the formulations, the methods of application, suchas foliar, drench, spraying, atomizing, dusting, scattering, coating orpouring, are chosen in accordance with the intended objectives and theprevailing circumstances.

The tank-mix compositions are generally prepared by diluting with asolvent (for example, water) the one or more pre-mix compositionscontaining different pesticides, and optionally further auxiliaries.

Suitable carriers and adjuvants can be solid or liquid and are thesubstances ordinarily employed in formulation technology, e.g. naturalor regenerated mineral substances, solvents, dispersants, wettingagents, tackifiers, thickeners, binders or fertilizers.

Generally, a tank-mix formulation for foliar or soil applicationcomprises 0.1 to 20%, especially 0.1 to 15%, of the desired ingredients,and 99.9 to 80%, especially 99.9 to 85%, of a solid or liquidauxiliaries (including, for example, a solvent such as water), where theauxiliaries can be a surfactant in an amount of 0 to 20%, especially 0.1to 15%, based on the tank-mix formulation.

Typically, a pre-mix formulation for foliar application comprises 0.1 to99.9%, especially 1 to 95%, of the desired ingredients, and 99.9 to0.1%, especially 99 to 5%, of a solid or liquid adjuvant (including, forexample, a solvent such as water), where the auxiliaries can be asurfactant in an amount of 0 to 50%, especially 0.5 to 40%, based on thepre-mix formulation.

Normally, a tank-mix formulation for seed treatment applicationcomprises 0.25 to 80%, especially 1 to 75%, of the desired ingredients,and 99.75 to 20%, especially 99 to 25%, of a solid or liquid auxiliaries(including, for example, a solvent such as water), where the auxiliariescan be a surfactant in an amount of 0 to 40%, especially 0.5 to 30%,based on the tank-mix formulation.

Typically, a pre-mix formulation for seed treatment applicationcomprises 0.5 to 99.9%, especially 1 to 95%, of the desired ingredients,and 99.5 to 0.1%, especially 99 to 5%, of a solid or liquid adjuvant(including, for example, a solvent such as water), where the auxiliariescan be a surfactant in an amount of 0 to 50%, especially 0.5 to 40%,based on the pre-mix formulation.

Whereas commercial products will preferably be formulated asconcentrates (e.g., pre-mix composition (formulation)), the end userwill normally employ dilute formulations (e.g., tank mix composition).

Preferred seed treatment pre-mix formulations are aqueous suspensionconcentrates. The formulation can be applied to the seeds usingconventional treating techniques and machines, such as fluidized bedtechniques, the roller mill method, rotostatic seed treaters, and drumcoaters. Other methods, such as spouted beds may also be useful. Theseeds may be presized before coating. After coating, the seeds aretypically dried and then transferred to a sizing machine for sizing.Such procedures are known in the art.

In general, the pre-mix compositions of the invention contain 0.5 to99.9 especially 1 to 95, advantageously 1 to 50, %, by mass of thedesired ingredients, and 99.5 to 0.1, especially 99 to 5, %, by mass ofa solid or liquid adjuvant (including, for example, a solvent such aswater), where the auxiliaries (or adjuvant) can be a surfactant in anamount of 0 to 50, especially 0.5 to 40, %, by mass based on the mass ofthe pre-mix formulation.

A compound of the formula (I) is in a preferred embodiment, independentof any other embodiments, is in the form of a plant propagation materialtreating (or protecting) composition, wherein said plant propagationmaterial protecting composition comprises additionally a colouringagent. The plant propagation material protecting composition or mixturemay also comprise at least one polymer from water-soluble andwater-dispersible film-forming polymers that improve the adherence ofthe active ingredients to the treated plant propagation material, whichpolymer generally has an average molecular weight of at least 10,000 toabout 100,000.

The combinations of the present invention (i.e. those comprising acompound of the present invention and one or more other biologicalactive agents) may be applied simultaneously or sequentially.

In the event, the ingredients of a combination are applied sequentially(i.e., one after the other), the ingredients are applied sequentiallywithin a reasonable period of each other to attain the biologicalperformance, such as within a few hours or days. The order of applyingthe ingredients in the combination, i.e., whether the compounds offormula (I) should be applied first or not is not essential for workingthe present invention.

In the event ingredients of the combinations are applied simultaneouslyin the present invention, they may be applied as a compositioncontaining the combination, in which case (A) the compound of formula(I) and the one or more other ingredients in the combinations can beobtained from separate formulation sources and mixed together (known asa tank-mix, ready-to-apply, spray broth, or slurry), or (B) the compoundof formula (I) and the one or more other ingredients can be obtained assingle formulation mixture source (known as a pre-mix, ready-mix,concentrate, or formulated product).

In an embodiment, independent of other embodiments, a compound accordingto the present invention is applied as a combination. Accordingly, thepresent invention also provides a composition comprising a a compoundaccording the invention as herein described and one or more otherbiological active agents, and optionally one or more customaryformulation auxiliaries; which may be in the form of a tank-mix orpre-mix composition.

Alternative to the actual synergistic action with respect to biologicalactivity, the combinations according to the invention also can havesurprising advantageous properties which can also be described, in awider sense, as synergistic activity. Examples of such advantageousproperties that may be mentioned are: advantageous behaviour duringformulation and/or upon application, for example upon grinding, sieving,emulsifying, dissolving or dispensing; increased storage stability;improved stability to light; more advantageous degradability; improvedtoxicological and/or ecotoxicological behaviour; or any other advantagesfamiliar to a person skilled in the art.

The compounds of the present invention may also find application inother fields, such as one or more of protection of stored goods andstore rooms, the protection of raw materials (such as wood andtextiles), floor coverings and buildings, and in hygienemanagement—especially the protection of humans, domestic animals andproductive livestock against pests. The invention therefore also makesavailable pesticidal compositions for such uses and the methodstherefor. The composition would need to be modified for use in aparticular use, and a skilled person would be able to make availablesuch compositions for any particular use.

In the hygiene sector, the compositions according to the invention areactive against ectoparasites such as hard ticks, soft ticks, mangemites, harvest mites, flies (biting and licking), parasitic fly larvae,lice, hair lice, bird lice and fleas.

Examples of such parasites are:

Of the order Anoplurida: Haematopinus spp., Linognathus spp., Pediculusspp. and Phtirus spp., Solenopotes spp.

Of the order Mallophagida: Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp. and Felicola spp.

Of the order Diptera and the suborders Nematocerina and Brachycerina,for example Aedes spp., Anopheles spp., Culex spp., Simulium spp.,Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp.,Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopotaspp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp.,Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossinaspp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp.,Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp.,Hippobosca spp., Lipoptena spp. and Melophagus spp.

Of the order Siphonapterida, for example Pulex spp., Ctenocephalidesspp., Xenopsylla spp., Ceratophyllus spp.

Of the order Heteropterida, for example Cimex spp., Triatoma spp.,Rhodnius spp., Panstrongylus spp.

Of the order Blattarida, for example Blatta orientalis, Periplanetaamericana, Blattelagermanica and Supella spp.

Of the subclass Acaria (Acarida) and the orders Meta- and Meso-stigmata,for example Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp.,Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp.,Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp.,Pneumonyssus spp., Sternostoma spp. and Varroa spp.

Of the orders Actinedida (Prostigmata) and Acaridida (Astigmata), forexample Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobiaspp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorusspp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp.,Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp.,Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp. andLaminosioptes spp.

The compositions according to the invention are also suitable forprotecting against insect infestation in the case of materials such aswood, textiles, plastics, adhesives, glues, paints, paper and card,leather, floor coverings and buildings. The compositions according tothe invention can be used, for example, against the following pests:beetles such as Hylotrupes bajulus, Chlorophorus pilosis, Anobiumpunctatum, Xestobium rufovillosum, Ptilinuspecticornis, Dendrobiumpertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctusafricanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens,Trogoxylon aequale, Minthesrugicollis, Xyleborus spec., Tryptodendronspec., Apate monachus, Bostrychus capucins, Heterobostrychus brunneus,Sinoxylon spec. and Dinoderus minutus, and also hymenopterans such asSirex juvencus, Urocerus gigas, Urocerus gigas taignus and Urocerusaugur, and termites such as Kalotermes flavicollis, Cryptotermes brevis,Heterotermes indicola, Reticulitermes flavipes, Reticulitermessantonensis, Reticulitermes lucifugus, Mastotermes darwiniensis,Zootermopsis nevadensis and Coptotermes formosanus, and bristletailssuch as Lepisma saccharina.

The application methods for applying a compound or a composition thereofto stored goods, store rooms, raw materials (such as wood and textiles),floor coverings and buildings, and in hygiene management is known in theart.

The invention also provides a method for treating, curing, controlling,preventing and protecting warm-blooded animals, including humans, andfish against infestation and infection by helminths, arachnids andarthropod endo- and ectoparasites which comprises orally, topically orparenterally administering or applying to said animals ananthelmintically, acaricidally or endo- or ectoparasiticidally effectiveamount of compound of formula (I).

The above method is particularly useful for controlling and preventinghelminth, nemtode, acarid and arthropod endo- and ectoparasiticinfestations and infections in warm-blooded animals such as cattle,sheep, swine, camels, deer, horses, poultry, fish, rabbits, goats, mink,fox, chinchillas, dogs and cats as well as humans.

In the context of control and prevention of infestation and infectionsin warm-blooded animals, compounds of invention are especially usefulfor the control of helminths and nematodes. Examples for helminths aremembers of the class Trematoda, commonly known as flukes or flatworms,especially members of the genera Fasciola, Fascioloides, Paramphistomu,Dicrocoelium, Eurytrema, Ophisthorchis, Fasciolopsis, Echinostoma andParagonimus. Nematodes which can be controlled by the formula (I)compounds include the genera Haemonchus, Ostertagia, Cooperia,Oesphagastomu, Nematodirus, Dictyocaulus, Trichuris, Dirofilaria,Ancyclostoma, Ascaria and the like.

The compound of this invention may also control endoparasitic arthropodinfestations such as cattle grub and stomach bot. In addition, acaridand arthropod ectoparasitic infestations in warm-blooded animals andfish including biting lice, sucking lice, bot flies, biting flies,muscoid flies, flies, myiasitic fly larvae, gnats, mosquitoes, fleas,mites, ticks, nasal bots, keds and chiggers may be controlled, preventedor eliminated by the compounds of this invention. Biting lice includemembers of Mallophaga such as Bovicola bovis, Trichodectes canis andDamilina ovis. Sucking lice include members of Anoplura such asHaematopinus eurysternus, Haematopinus suis, Linognathus vituli andSolenopotes capillatus. Biting flies include members of Haematobia.Ticks include Boophilus, Rhipicephalus, Ixodes, Hyalomma, Amblyomma andDermacentor. The compounds of the invention may also be used to controlmites which are parasitic on warm-blooded mammals and poultry includingmites of the orders Acariformes and Parasitiformes.

For oral administration to warm-blooded animals, the compounds of theinvention may be formulated as animal feeds, animal feed premixes,animal feed concentrates, pills, solutions, pastes, suspensions,drenches, gels, tablets, boluses and capsules. In addition, thecompounds of the invention may be administered to the animals in theirdrinking water. For oral administration, the dosage form chosen shouldprovide the animal with about 0.01 mg/kg to 100 g/kg of animal bodyweight per day of the compound of the invention.

Alternatively, the compounds of the invention may be administered toanimals parenterally, for example, by intraruminal, intramuscular,intravenous or subcutaneous injection. The compounds of the inventionmay be dispersed or dissolved in a physiologically acceptable carrierfor subcutaneous injection. Alternatively, the compounds of theinvention may be formulated into an implant for subcutaneousadministration. In addition the compounds of the invention may betransdermally administered to animals. For parenteral administration,the dosage form chosen should provide the animal with about 0.01 mg/kgto 100 mg/kg of animal body weight per day of the compound of theinvention.

The compounds of the invention may also be applied topically to theanimals in the form of dips, dusts, powders, collars, medallions, spraysand pour-on formulations. For topical application, dips and spraysusually contain about 0.5 ppm to 5,000 ppm and preferably about 1 ppm to3,000 ppm of the compound of the invention. In addition, the compoundsof the invention may be formulated as ear tags for animals, particularlyquadrupeds such as cattle and sheep.

The compounds of the invention may also be used in combination orconjunction with one or more other parasiticidal compounds (to broadenthe spectrum of activity) including, but not limited to, anthelmintics,such as benzimidazoles, piperazine, levamisole, pyrantel, praziquanteland the like; endectocides such as avermectins, milbemycins and thelike; ectoparasiticides such as arylpyrroles, organophosphates,carbamates, gamabutyric acid inhibitors including fipronil, pyrethroids,spinosads, imidacloprid and the like; insect growth regulators such aspyriproxyfen, cyromazine and the like; and chitin synthase inhibitorssuch as benzoylureas including flufenoxuron.

The parasiticidal compositions of the present invention include aparasiticidally effective amount of a compound of the invention orcombinations thereof admixed with one or more physiologically tolerableinert, solid or liquid carriers known from veterinary medicinal practicefor oral, percutaneous and topical administration. Such compositions maycomprise further additives, such as stabilizers, anifoams, viscosityregulators, binders and tackifiers, whereas commercial products willpreferably be formulated as concentrates, the end user will normallyemploy dilute formulations.

The compositions according to the present invention may also be used forthe preparation of composition useful to curatively or preventivelytreat human and animal fungal diseases such as, for example, mycoses,dermatoses, trichophyton diseases and candidiases or diseases caused byAspergillus spp., for example Aspergillus fumigatus.

In an embodiment, independent of any other embodiments, a compound offormula (I) is a anti-helminth compound.

In an embodiment, independent of any other embodiments, a compound offormula (I) is a pesticidal compound, preferably a nematicidal compound.

In each aspect and embodiment of the invention, “consisting essentially”and inflections thereof are a preferred embodiment of “comprising” andits inflections, and “consisting of” and inflections thereof are apreferred embodiment of “consisting essentially of” and its inflections.

The disclosure in the present application makes available each and everycombination of embodiments disclosed herein.

The following Examples serve to illustrate the invention. They do notlimit the invention. Temperatures are given in degrees Celsius; mixingratios of solvents are given in parts by volume.

EXAMPLES Preparation Example 1 3-Methyl-pyridine-2-carboxylic acid(1-o-Tolyl-cyclopropylmethyl)-amide (Compound A.9) Step 1:C-(1-o-Tolyl-cyclopropyl)-methylamine (Compound Q.1)

4.56 g of 1-o-tolyl-cyclopropanecarbonitrile was dissolved in 150 ml ofmethanol and 40 ml of ammonia (7N solution in methanol) was added,followed by 4.5 g of Raney Nickel. The reactor was sealed and thereaction mixture was stirred under 1 bar of hydrogen at ambienttemperature for 2 days. Then the reaction mixture was filtered overcelite and the filtrate was concentrated. The residue was purified bychromatography on silica gel, with ethyl acetate/methanol/triethylamine(90:5:5) as a eluent. Thus, 4.01 g C-(1-o-tolylcyclopropyl)-methylaminewas obtained as an oil. ¹H-NMR (CDCl₃): 7.25 ppm (m, 1H), 7.13 ppm (m,3H), 2.70 ppm (s, 2H), 2.41 ppm (s, 3H), 1.40 ppm (s, 2H, broad), 0.80ppm (m, 4H).

Step 2: 3-Methyl-pyridine-2-carboxylic acid(1-o-tolyl-cyclopropylmethyl)-amide (Compound A.9)

150 mg of C-(1-o-tolyl-cyclopropyl)-methylamine (step 1) was dissolvedin 5 ml of dichloromethane and cooled to 0° C. Then 188 mg oftriethylamine was added, followed by dropwise addition of a solution of145 mg of 3-methyl-pyridine-2-carbonyl chloride in 1 ml dichloromethane.The reaction mixture was stirred at ambient temperature for 3 days. Then6 ml of water were added, the resulting phases were separated and theorganic phase was washed with aqueous 2N sodium hydroxide solution, thenwith 1N aqueous hydrochloric acid and brine, dried over sodium sulfate,filtered and concentrated. The residue was purified by chromatography onsilica gel with cyclohexane/ethyl acetate (5:1) as a eluent. Thus, 51 mgof 3-methyl-pyridine-2-carboxylic acid(1-o-tolylcyclopropylmethyl)-amide was obtained as an oil. ¹H-NMR(CDCl₃): 8.83 ppm (m, 1H), 8.15 ppm (s, 1H, broad), 7.55 ppm (m, 1H),7.30 ppm (m, 1H), 7.27 ppm (m, 1H), 7.12 ppm (m, 3H), 3.55 (d, 2H), 2.70ppm (s, 3H), 2.50 ppm (s, 3H), 1.02 ppm (m, 2H), 0.82 ppm (m, 2H).

Preparation Example 2N-[[1-(4-cyano-2,6-difluoro-phenyl)cyclopropyl]methyl]-2-(trifluoromethyl)benzamide(Compound A.57)

N-[[1-(4-bromo-2,6-difluoro-phenyl)cyclopropyl]nethyl]-2-(trifluoromethyl)benzamide(100 mg) and Zn(CN)2 (16.2 mg) were dissolved in deoxygenated DMF underan inert atmosphere. Pd(PPh3)4 (13.5 mg) was added and the vial wasclosed under inert atmosphereand placed in a preheated 80° C. oil bathand stirred for 2.5 hrs. TLC shows only traces of product. Pd(PPh3)4(13.5 mg) and Zn(CN)2 (16.2 mg) were added and the reaction mixture wasstirred overnight at 80° C. TLC shows only traces of product, Pd(PPh3)4(27 mg) and Zn(CN)2 (32.4 mg) were added and the RM was stirred at 100°C. to form a yellow solution with white precipitate. TLC shows almostcomplete conversion. The reaction mixture was cooled down to RT anddiluted with toluene, washed 2 times with 2 M NH4OH solution and brine,dried over Na2SO4 and the solvent was evaporated to give 145 mg of ayellow oil. Preperative TLC: hexanes:EtOAc 4:1

Yielded 71.7 mg of product which crystallised to a yellow solid m.p.100-102° C.

¹H-NMR (CDCl₃): 8.72 (d, 1H); 8.26 (d, 1H); 7.89 (br s, 1H); 7.58 (dd,1H); 7.15 (m, 2H); 3.63 (d, 2H); 1.16 (t, 2H); 0.98 (t, 2H).

Preparation Example 3N-[[1-(4-cyclopropyl-2,6-difluoro-phenyl)cyclopropyl]methyl]-2-(trifluoromethyl)benzamide(Compound A.58)

ToN-[[1-(4-bromo-2,6-difluoro-phenyl)cyclopropyl]methyl]-2-(trifluoromethyl)benzamide(100 mg), cyclopropylboronic acid (66 mg), P(Cy)3 (13 mg), and K3PO4(349 mg) in toluene (1.5 ml) and water (0.04 ml) was added Pd(OAc)2 (5.3mg) under an inert atmosphere. The reaction mixture was heated to 100°C. for 22 hrs. EtOAc and water were added and the phases were separated.The organic layer was washed with brine, dried over Na2SO4 andconcentrated to give 210 mg of light brown oil. Preperative TLC(hexanes/EtOAc 9:1, 7 times eluted): yielded 165.4 mg of the product asyellow oil,

¹H-NMR (CDCl₃): 8.73 (d, 1H); 8.12 (d, 1H); 7.89 (br s, 1H); 7.53 (dd,1H); 6.53 (m, 2H); 3.55 (d, 2H); 1.82 (m, 1H); 1.08-0.86 (m, 6H); 0.63(m, 2H)

Preparation Example 4N-[[1-(2,4,6-trichlorophenyl)cyclopropyl]methyl]-3-(trifluoromethyl)pyridine-2-carboxamide(Compound A29) Step 1: 1,3,5-trichloro-2-(chloromethyl)benzene

To a stirred solution of (2,4,6-trichlorophenyl)methanol (2 g, 9.4574mmol) in chloroform (20 mL) kept under N2 atmosphere, thionyl chloride(1.25 mL, 17.023 mmol), was added slowly at 0° C. over a period of 10min followed by a catalytic amount of DMF (35 mg, 0.4733 mmol). Thereaction mixture was allowed to stirred at RT for 2 h.

The reaction mixture was quenched with 10 mL of water; the aqueous layeris extracted with dichloromethane (3 times). The combined organic layerwere washed with 5% Na2CO3 solution (2*10 mL), followed by NaCl (10 mL)and dried over Na2SO4. The solvent was evaporated under reduced pressureto give an yellow oil (1.78 gr). The oil was diluted in EtOAc and washedtwice with NaCl (3 mL), then dried over NaSO4, filtrated and evaporatedto give 1.58 g of desired product.

¹H-NMR (CDCl₃): 7.4 (s, 2H); 4.8 (s, 2H).

Step 2: 2-(2,4,6-trichlorophenyl)acetonitrile

To a stirred solution of 1,3,5-trichloro-2-(chloromethyl)benzene (1.7 g,7.39 mmol) in EtOH (5.7 mL), NaCN (0.411 g, 8.13 mmol) in H2O (1.7 mL)was added at RT. The reaction mixture was refluxed for 4 hr to completethe reaction.

EtOH was evaporated and the white solid was diluted in water (6 mL). Theaqueous layer was extracted with EtOAc (3 times). The combined organiclayer were washed with NaCl (10 mL) and dry over Na2SO4. The solvent wasevaporated under reduced pressure to give a white solid (1.585 gr)

The crude was purified by flash chromatography (Cyclohexane/EtOAc (NB):100% of A to 50% of B) to give 1.098 g of desired product.

¹H-NMR (CDCl₃): 7.45 (s, 2H); 3.95 (s, 2H).

Step 3: 1-(2,4,6-trichlorophenyl)cyclopropanecarbonitrile

To a solution of NaH 60% in oil (0.387 g, 9.67 mmol) in dry THF (1.5 mL)was added dropwise, under argon, at 0° C. a solution of2-(2,4,6-trichlorophenyl)acetonitrile (0.748 g, 3.22 mmol), in THF (1.5mL). The yellow mixture was stirred until the end of gaz formation. Then1,2-dibromoethane (2.45 g, 12.9 mmol) was added dropwise at 0° C. Thereaction mixture was stirred 30 min at 0° C. then allowed at RT-2 hr.

The reaction mixture was quenched at 0° C. with aq NH4Cl (12 mL). EtOAcwas added. The phases were separated. The water phase was extractedagain with EtOAc. The combined organic phases were dried with Na₂SO₄filtrated and the organic phases evaporated to give a pink solid (1.42g) which was purified by flash chromatography (Solvent:Cyclohexane/EtOAc 4/1) to give a white solid (0.704 g).

¹H-NMR (CDCl₃): 7.4 (s, 2H); 1.95 (m, 2H), 1.45 (m, 2H).

Step 4: [1-(2,4,6-trichlorophenyl)cyclopropyl]methanamine

To a solution of 1-(2,4,6-trichlorophenyl)cyclopropanecarbonitrile(0.702 g, 2.85 mmol) in Et2O (6 mL), was added carefully, at 0° C.,LiAlH4 (1 M) in Et2O (4.27 mL, 4.27 mmol) (exothermic, keep T° between5-10° C.). The suspension was stirred 1 hr at 0° C. Then the reactionmixture was diluted, 6 mL of Et2O was added, then quenched at 0° C. verycarefully with 3 ml water (exothermic, react violently, gaz), then 6 mLaq. NaOH 4 M, then 9 mL water. The reaction mixture was stirred 10 minat RT, then Na2SO4 was added and the reaction mixture was stirred 5 minmore. All salts were filtrated over celite. The organic phase was washedwith brine. The organic layer was dried with Na₂SO₄, filtrated and theorganic phase evaporated to give a yellow oil (524 mg).

¹H-NMR (CDCl₃): 7.35 (s, 2H); 2.85 (s, 2H), 1.6 (bs, 2H), 1.0 (m, 2H),0.95 (m, 2H).

Step 5:N-[[1-(2,4,6-trichlorophenl)cyclopropyl]methyl]-3-(trifluoromethyl)pyridine-2-carboxamide(Compound A29)

To a solution of [1-(2,4,6-trichlorophenyl)cyclopropyl]methanamine (1.10mL, 0.458 mmol) in dry dichloromethane (1.8 mL) was added, under argon,Et3N (0.129 mL, 0.915 mmol), then the mixture was cooled at 0° C. Thenwere added EDCl.HCl (0.175 g, 0.915 mmol), HOBT.H2O (0.125 g, 0.915mmol), 3-(trifluoromethyl)pyridine-2-carboxylic acid (0.0874 g, 0.458mmol) and the reaction mixture was stirred ON at RT. Water was added,the aqueous solution was extracted with dichloromethane (3 times), thecombined organic layers were washed by NaCl, dried over Na2SO4,filtrated and evaporated under reduced pressure to give yellow oil (198mg). The crude was purified by flash chromatography using silica gel(Cyclohexane to Cyclohexane/AcOEt:1/4) afforded the desired product aswhite solid (115.7 mg).

¹H-NMR (CDCl₃): 8.7 (d, 1H); 8.15 (d, 1H), 8.0 (bs, 1H), 7.55 (m, 1H),7.3 (s, 2H), 3.67 (d, 2H), 1.25 (m, 2H), 1.05 (m, 2H).

Preparation Example 53-chloro-N-[[1-[2-Fluoro-4-(trifluoromethyl)phenyl]cyclopropyl]methyl]pyridine-2-carboxamide(Compound A37) Step 1:1-[2-fluoro-4-(trifluoromethyl)phenyl]cyclopropanecarbonitrile

2-Fluoro-4-(trifluoromethyl)phenylacetonitrile (3 g, 14.47 mmol) wasdissolved in THF (30 mL). Sodium hydride (1.7366 g, 43.42 mmol) wasadded in several portions at 0° C. The reaction mixture was stirreduntil no detectable gas evolution. The reaction mixture was then a redsuspension. At 0° C. 1-Bromo-2-chloro-ethane (4.80 mL, 57.89 mmol) wasadded drop wise. The reaction mixture was stirred 30 min at 0° C. then 2h at 50° C. It was cooled down to rt. The suspension was filtrated overHyflo. The filtrate was evaporated. The residue was 3.7 g dark redliquid/oil. The crude was purified by flash chromatography (Solvent:Cyclohexane/EtOAc 1/1) to yield 1.81 g of a yellow oil, the desiredproduct.

¹H-NMR (CDCl₃): 7.5 (t, 1H), 7.45-7.35 (m, 2H), 1.75 (m, 2H), 1.45 (m,2H).

Step 2: [1-[2-fluoro-4-(trifluoromethyl)phenyl]cyclopropyl]methanamine

To a solution of1-[2-fluoro-4-(trifluoromethyl)phenyl]cyclopropanecarbonitrile (1.926 g,8.404 mmol) in Et2O (20 mL, 8.404 mmol), was added carefully, at 0° C.,LiAlH4 (1 M) in Et2O (6.723 mL, 6.723 mmol) (exothermic, keep T° between5-10° C.). The colorless solution had turn to an orange suspension whichwas stirred 1 h at 0° C. As there was some starting material left, 1.6mL of LiAlH4 (1 M in Et2O) was added and the reaction mixture wasstirred one more hour. Then the reaction mixture was diluted, 20 mL ofEt2O was added, then quenched at 0° C. very carefully with 6 mL water(exothermic, react violently, gaz), then 5 mL aq. NaOH 2 M, then 6 mLwater. The reaction mixture was stirred 10 min at RT, then Na2SO4 wasadded and the reaction mixture was stirred 5 min more. All salts werefiltrated over celite. The filtrate was washed with brine. The organiclayer was dried with Na2SO4, filtrated and evaporated to give an yellowoil (1.66 g) which was the desired product.

¹H-NMR (CDCl₃): 7.44 (t, 1H), 7.37 (d, 1H), 7.30 (d, 1H), 2.80 (s, 2H),1.15 (bs, 2H), 0.84 (m, 4H).

Step 3:3-chloro-N-[[1-[2-fluoro-4-(trifluoromethyl)phenyl]cyclopropyl]methyl]pyridine-2-carboxamide(Compound A37)

To a solution of[1-[2-fluoro-4-(trifluoromethyl)phenyl]cyclopropyl]methanamine (0.500mL, 0.510 mmol) in dry dichloromethane (2.0 mL, 0.510 mmol) was added,under argon, Et3N (0.144 mL, 1.02 mmol), then the mixture was cooled at0° C. There were added EDCl.HCl (0.196 g, 1.02 mmol), HOBT.H2O (0.139 g,1.02 mmol), 3-chloropyridine-2-carboxylic acid (0.0803 g, 0.510 mmol)and the reaction mixture was stirred overnight at RT. Water was added,the aqueous solution was extracted with dichloromethane (3 times), thecombined organic layers were washed by NaCl, dried over Na2SO4,filtrated and evaporated under reduced pressure to give an oil (0.316mg). which was purified by flash chromatography (Cyclohexane toCyclohexane/AcOEt:4/1). The desired compound was isolated as a colorlessoil (143.0 mg).

¹H-NMR (CDCl₃): 8.43 (d, 1H), 7.88 (bs, 1H), 7.80 (d, 1H), 7.46 (t, 1H),7.40-7.30 (m, 3H), 3.63 (d, 2H), 1.10 (m, 2H), 0.91 (m, 2H).

According to the methods described above, the compounds in Table A & Qwere prepared.

TABLE A Compounds of formula (I). (I)

Re- tent- ion [M + Method Mp R1 R2 R3 R4 R5 R6 R7 A1 A2 A3 A4 A5 timeH]⁺ LC-MS (° C.) A.1 H H H H

H H C—CH3 C—H C—H C—CH3 C—H 1.89 314/ 316 ZCQ11 A.2 H H H H

H H N C—H C—H C—H N 1.56 268 ZMD11 A.3 H H H H

H H C—Cl C—H C—H C—H N 1.72 321/ 323/ 325 ZCQ11 A.4 H H H H

H H C—Cl C—H C—H C—H N 1.75 301/ 303 ZMD11 A.5 H H H H

H H C—CH3 C—CH3 C—H C—H C—H 1.86 314/ 316 ZCQ11 110- 113 A.6 H H H H

H H C—CH3 C—H C—H C—CH3 C—H 1.86 294 ZMD11 A.7 H H H H

H H N C—H C—H C—H N 1.54 288/ 290 ZCQ11 A.8 H H H H

H H C—CH3 C—H C—CH3 C—H C—H 1.89 314/ 316 ZCQ11 109- 114 A.9 H H H H

H H C—CH3 C—H C—H C—H N 1.82 281 ZMD11 A.10 H H H H

H H C—CH3 C—H C—CH3 C—H C—H 1.89 294 ZMD11 104- 106 A.11 H H H H

H H C—CH3 C—CH3 C—H C—H C—H 1.88 294 ZMD11 95-99 A.12 H H H H

H H C—CH3 C—H C—H C—H N 1.82 301/ 303 ZCQ11 A.13 H H H H

H H C—F C—H C—H C—H N 48-49 A.14 H H H H

H H C—Cl C—H C—H C—H N 97-98 A.15 H H H H

H H C—F C—H C—H C—H N oil A.16 H H H H

H H C—Cl C—H C—H C—H N 69-71 A.17 H H H H

H H C—Cl C—H C—H C—H N 79-81 A.18 H H H H

H H C—F C—H C—H C—H N oil A.19 H H H H

H H C—F C—H C—H C—H N 98-99 A.20 H H H H

H H C—Cl C—H C—H C—H N 93-94 A.21 H H H H

H H C—CF3 C—H C—H C—H N 1.02 438   STAND- ARD A.22 H H H H

H H C—Cl C—H C—H C—H N 0.98 340.9 STAND- ARD 128- 129 A.23 H H H H

H H C—CF3 C—H C—H C—H N 1.03 375   STAND- ARD 106- 107 A.24 H H H H

H H C—Cl C—H C—H C—H N 0.99 340.9 STAND- ARD 79-80 A.25 H H H H

H H C—F C—H C—H C—H N 0.96 325   STAND- ARD 90-91 A.26 H H H H

H H C—F C—H C—H C—H N 0.98 325   STAND- ARD A.27 H H H H

H H C—Br C—H C—H C—H N 0.99 373.9 STAND- ARD 124- 125 A.28 H H H H

H H C—Br C—H C—H C—H N 1   386.9 STAND- ARD  99- 100 A.29 H H H H

H H C—CF3 C—H C—H C—H N 1.19 425   STAND- ARD 142- 144 A.30 H H H H

H H C—F C—H C—H C—H N 1.12 375   STAND- ARD A.31 H H H H

H H C—CF3 C—H C—H C—H N 1.08 391   STAND- ARD A.32 H H H H

H H C—F C—H C—H C—H N 1.02 341   STAND- ARD A.33 H H H H

H H C—Cl C—H C—H C—H N 1.03 357   STAND- ARD A.34 H H H H

H H C—CF3 C—H C—H C—H N 1.14 475   STAND- ARD  99- 100 A.35 H H H H

H H C—CF3 C—H C—H C—H N 1.11 389   STAND- ARD 111- 112 A.36 H H H H

H H C—CF3 C—H C—H C—H N 1.09 407   STAND- ARD A.37 H H H H

H H C—Cl C—H C—H C—H N 1.03 373   STAND- ARD A.38 H H H H

H H C—F C—H C—H C—H N 1.03 357   STAND- ARD A.39 H H H H

H H C—Cl C—H C—H C—H N 1.1  374   STAND- ARD A.40 H H H H

H H C—Br C—H C—H C—H N 1.1  419   STAND- ARD A.41 H H H H

H H N C—CF3 C—H C—H C—H 1.2  423   STAND- ARD A.42 H H H H

H H C—Cl C—H C—H C—H N 1.08 389   STAND- ARD A.43 H H H H

H H C—Br C—H C—H C—H N 1.11 434   STAND- ARD A.44 H H H H

H H C—CF3 C—H C—H C—H N 1.11 407   STAND- ARD A.45 H H H H

H H C—Cl C—H C—H C—H N 1.08 356   STAND- ARD A.46 H H H H

H H C—Br C—H C—H C—H N 1.08 401   STAND- ARD A.47 H H H H

H H C—F C—H C—H C—H N 1.07 373   STAND- ARD A.48 H H H H

H H C—CF3 C—H C—H C—H N 1.02 424   STAND- ARD A.49 H H H H

H H C—Cl C—H C—H C—H N 1.83 355/ 357 ZDQ11 A.50 H H H H

H H C—F C—H C—H C—H N 1.81 339/ 341 ZDQ11 A.51 H H H H

H H C—F C—H C—H C—H N 83-84 A.52 H H H H

H H C—F C—H C—H C—H N 1.04 311   ZDQ12 A.53 H H H H

H H C—F C—H C—H C—H N 0.84 296   ZDQ12 A.54 H H H H

H H C—CF3 C—H C—H C—H N 122- 124 A.55 H H H H

H H C—F C—H C—H C—H N 0.89 337   ZDQ12 A.56 H H H H

H H C—F C—H C—H C—H N 0.99 285   ZDQ12 A.57 H H H H

H H C—CF3 C—H C—H C—H N 100- 102 A.58 H H H H

H H C—CF3 C—H C—H C—H N 1.11 397   ZDQ12 A.59 H H H H

H H C—CF3 C—H C—H C—H N 143- 145 A.60 H H H H

H H C—CF3 C—H C—H C—H N 126- 128 A.61 H H H H

H H C—CF3 N C—H C—H C—H 120- 121 A.62 H H H H

H H C—F C—H C—H C—H C—F 94-96 A.63 H H H H

H H C—CF3 C—H C—H C—H C—H 97-99 A.64 H H H H

H H C—CF3 C—H C—H C—H C—H 68-71 A.65 H H H H

H H C—CF3 C—H C—H C—H C—H 96-97 A.66 H H H H

H H C—Cl N C—H C—H N 1.71 342   STAND- ARD A.67 H H H H

H H C—CF3 C—H C—H C—H C—H 113- 114 A.68 H H H H

H H C—Cl N C—H C—H N 98-99 A.69 H H H H

H H C—Cl N C—H C—H N 112- 113 A.70 H H H H

H H C—CF3 C—H C—H C—H C—H 102- 103 A.71 H H H H

H H C—F C—H C—H C—H C—F 100- 103 A.72 H H H H

H H C—F C—H C—H C—H C—F 82-84 A.73 H H H H

H H C—CF3 C—H C—H C—H C—H 73-75 A.74 H H H H

H H C—F C—H C—H C—H C—F 125- 127 A.75 H H H H

H H C—CF3 C—H C—H C—H C—H 73-75 A.76 H H H H

H H C—CF3 C—H C—H C—H C—H 76-78 A.77 H H H H

H H C—Cl C—H N C—H N 96-97 A.78 H H H H

H H C—Cl C—H N C—H N 97-98 A.79 H H H H

H H C—CF3 C—H C—H C—H C—H 95-97 A.80 H H H H

H H C—CF3 N C—H C—H C—H 145- 177 A.81 H H H H

H H C—Cl N C—H C—H N 0.88 372/ 374 STAND- ARD A.82 H H H H

H H C—CF3 C—H C—H C—H C—H 1.09 390   STAND- ARD A.83 H H H H

H H C—CF3 N C—H C—H C—H 1.02 391   STAND- ARD A.84 H H H H

H H C—Cl N C—H C—H N 1   358   STAND- ARD A.85 H H H H

H H C—Cl C—H N C—H N 110- 111 A.86 H H H H

H H C—F C—H C—H C—H C—F 132- 133 A.87 H H H H

H H C—CF3 C—H C—H C—H C—H 1.18 422   STAND- ARD A.88 H H H H

H H C—CF3 C—H C—H C—H C—H 129- 130 A.89 H H H H

H H C—S—CH3 C—H C—H C—H N 1.1  379   ZDQ12 A.90 H H H H

H H C—SO2—CH3 C—H C—H C—H N 37-39 A.91 H H H H

H H C—SO2—CH3 C—H C—H C—H N 47-49 A.92 H H H H

H H C—CF3 N C—H C—H C—H 127- 128 A.93 H H H H

H H C—F C—H C—H C—H C—F 1.06 374   STAND- ARD A.94 H H H H

H H C—Cl N C—H C—H N 97-98 A.95 H H H H

H H C—Cl C—H N C—H N 1.05 356   STAND- ARD A.96 H H H H

H H C—Cl C—H N C—H N 1.08 356   STAND- ARD A.97 H H H H

H H C—Cl C—H N C—H N 1.07 391   STAND- ARD A.98 H H H H

H H C—CF3 C—H C—H C—H C—H 89-92 A.99 H H H H

H H C—Br N C—H C—H C—H 1.02 399   STAND- ARD A.100 H H H H

H H C—F N C—H C—H C—H 1.04 339   STAND- ARD A.101 H H H H

H H C—F C—H C—H C—H C—F 100- 102 A.102 H H H H

H H C—CF3 C—H C—H C—H C—H 1.02 356   ZDQ12 A.103 H H H H

H H C—CF3 C—H N C—H N 101- 103 A.104 H H H H

H H C—CF3 N C—H N C—H 146- 146 A.105 H H H H

H H C—CF3 C—H C—H N N 117- 119 A.106 H H H H

H H C—CF3 N N C—H C—H 137- 139 A.107 H H H H

H H C—CF3 C—H N N C—H 1.03 390   STAND- ARD A.108 H H H H

H H C—CF3 N C—H C—H N 97-99 A.109 H H H H

H H C—CF3 C—H N C—H N 1.05 408   STAND- ARD A.110 H H H H

H H C—CF3 N C—H N C—H 134- 136 A.111 H H H H

H H C—CF3 C—H C—H C—H N 1.14 479   ZDQ12 A.112 H H H H

H H C—Cl C—H C—H C—H N 1.12 445   ZDQ12 A.113 H H H H

H H C—CF3 N C—H C—H C—H 0.94 357   STAND- ARD A.114 H H H H

H H C—CF3 N C—H C—H N 0.97 358   STAND- ARD A.115 H H H H

H H C—CF3 C—H C—H C—H N 0.99 357   STAND- ARD A.116 H H H H

H H C—Cl C—H C—H C—H N 123- 124 A.117 H H H H

H H C—CF3 C—H C—H C—H N 155- 157 A.118 Me H H H

H H C—CF3 C—H C—H C—H N 1.08 371   ZDQ12 A.119 H H H H

H H C—CF3 C—H C—H C—H N 1.07 373   ZDQ12 A.120 H H H H

Me H C—CF3 C—H C—H C—H N 1.14 414   ZDQ12 A.121 H H H H

H H C—CF3 C—H C—H C—H N 1.09 418   ZDQ12

TABLE Q Compounds of formulae (II) (II)

CAS Retention Method Mp Formula Reference R1 R2 R3 R4 R5 R6 R7 time [M +H]+ LC-MS (° C.) Q.1 Formula (II) 886365-78-2 H H H H

H H 0.56 162 ZMD11 Q.2 Formula (II) 886365-68-0 H H H H

H H 0.76 182/184 ZCQ11 Q.3 Formula (II) — H H H H

H H Q.4 Formula (II) 69385-29-1 H H H H

H H Q.5 Formula (II) 75180-46-0 H H H H

H H Q.6 Formula (II) — H H H H

H HZQ Mass Spectrometer from Waters (Single Quadrupole Mass Spectrometer)Instrument Parameter:Ionization method: ElectrosprayPolarity: positive and negative ionsCapillary: 3.00 kVCone: 30.00 VExtractor: 2.00 VSource Temperature: 100° C.,Desolvation Temperature: 250° C.Cone Gas Flow: 50 L/HrDesolvation Gas Flow: 400 L/HrMass range: 100 to 900 DaHP 1100 HPLC from Agilent:Solvent degasser, binary pump, heated column compartment and diode-arraydetector.Column: Phenomenex Gemini C18, 3 □m, 30×3 mm,Temp: 60° C.DAD Wavelength range (nm): 210 to 500Solvent Gradient:A=H2O+5% MeOH+0.05% HCOOHB=Acetonitril+0.05% HCOOH

Time A % B % Flow (ml/min) 0.00 100 0 1.700 2.00 0 100.0 1.700 2.80 0100.0 1.700 2.90 100 0 1.700 3.00 100 0 1.700ZQ Mass Spectrometer from Waters (Single Quadrupole Mass Spectrometer)Instrument Parameter:Ionization method: ElectrosprayPolarity: positive and negative ionsCapillary: 3.00 kVCone: 30 VExtractor: 2.00 VSource Temperature: 150° C.,Desolvation Temperature: 350 CCone Gas Flow: 50 L/HrDesolvation Gas Flow: 400 L/HrMass range: 100 to 900 DaAcquity UPLC from Waters:Binary pump, heated column compartment and diode-array detector.Solvent degasser, binary pump, heated column compartment and diode-arraydetector.Column: Waters UPLC HSS T3, 1.8 □m, 30×2.1 mm,Temp: 60° C.DAD Wavelength range (nm): 210 to 500Solvent Gradient:A=H2O+5% MeOH+0.05% HCOOHB=Acetonitril+0.05% HCOOH

Time A % B % Flow (ml/min) 0.00 90 10 0.85 1.20 0 100.0 0.85 1.50 0100.0 0.85ZQ Mass Spectrometer from Waters (Single Quadrupole Mass Spectrometer)Instrument Parameter:Ionization method: ElectrosprayPolarity: positive and negative ionsCapillary: 3.00 kVCone: 30.00 VExtractor: 2.00 VSource Temperature: 100° C.,Desolvation Temperature: 250° C.Cone Gas Flow: 50 L/HrDesolvation Gas Flow: 400 L/HrMass range: 100 to 900 DaHP 1100 HPLC from Agilent:Solvent degasser, quaternary pump, heated column compartment anddiode-array detector.Column: Phenomenex Gemini C18, 3 mm, 30×3 mm,Temp: 60° C.DAD Wavelength range (nm): 210 to 500Solvent Gradient:A=H2O+5% MeOH+0.05% HCOOHB=Acetonitril+0.05% HCOOH

Time A % B % Flow (ml/min) 0.00 100 0 1.700 2.00 0 100.0 1.700 2.80 0100.0 1.700 2.90 100 0 1.700 3.00 100 0 1.700ZMD Mass Spectrometer from Waters (Single Quadripole Mass Spectrometer)Instrument Parameter:Ionization method: ElectrosprayPolarity: positive or negative ionsCapillary: 3.80 kVCone: 30.00 VExtractor: 3.00 VSource Temperature: 150° C.,Desolvation Temperature: 350° C.Cone Gas Flow: OFFDesolvation Gas Flow: 600 L/HrMass range: 100 to 900 DaHP 1100 HPLC from Agilent:Solvent degasser, binary pump, heated column compartment and diode-arraydetector.Column: Phenomenex Gemini C18, 3 mm, 30×3 mm,Temp: 60° C.DAD Wavelength range (nm): 200 to 500Solvent Gradient:A=H2O+5% MeOH+0.05% HCOOHB=Acetonitril+0.05% HCOOH

Time A % B % Flow (ml/min) 0.00 100 0 1.700 2.00 0 100.0 1.700 2.80 0100.0 1.700 2.90 100 0 1.700 3.00 100 0 1.700ZQ Mass Spectrometer from Waters (Single Quadrupole Mass Spectrometer)Instrument Parameter:Ionization method: ElectrosprayPolarity: positive and negative ionsCapillary: 3.00 kVCone: 30 VExtractor: 2.00 VSource Temperature: 150° C.,Desolvation Temperature: 350 CCone Gas Flow: 50 L/HrDesolvation Gas Flow: 400 L/HrMass range: 100 to 900 DaAcquity UPLC from Waters:Binary pump, heated column compartment and diode-array detector.Solvent degasser, binary pump, heated column compartment and diode-arraydetector.Column: Waters UPLC HSS T3, 1.8 □m, 30×2.1 mm,Temp: 60° C.DAD Wavelength range (nm): 210 to 500Solvent Gradient:A=H2O+5% MeOH+0.05% HCOOHB=Acetonitril+0.05% HCOOH

Time A % B % Flow (ml/min) 0.00 90 10 0.85 1.20 0 100.0 0.85 1.50 0100.0 0.85

BIOLOGICAL EXAMPLES

Meloidogyne spp. (Root-Knot Nematode) Contact Activity, Preventive.Pouch Test

Filter papers (9 cm×4.5 cm) with a small pocket were placed into plasticpouches (12 cm×6 cm). One cucumber cv. Toshka seed was placed in thecentre of the filter paper pocket of all the pouches needed for a test.The cucumber seeds in the pouches were treated with test solutions at200 ppm by pipetting the solution directly over the cucumber seed in thefilter paper pocket in the pouch. Prior to application, the compoundsolution was prepared at twice the concentration required and the eggsuspension is prepared with FORL nutrient solution with 3000 eggs/0.5ml. After applying all the treatments, 3000 eggs (in 0.5 ml of FORLnutrient solution) were pipetted into the pouches. The pouches wereincubated in a moist chamber for twelve days and watered regularly tomaintain good filter paper moisture essential for the growing cucumberroot system. After this period, the filter paper containing thegerminated cucumber seedling was removed from the plastic pouch toassess the number of galls caused by Meloidogyne spp. per root system.

The following compounds showed a greater than 75% reduction of gallingcompared to the untreated control: A.1, A.2, A.3, A.5, A.6, A.7, A.9,A.11, A.12, A.15, A.18, A.65, A.66, A.67, A.68, A.69, A.70, A.73, A.77,A.84, A.85, A.94, A.101.

Meloidogyne spp. (Root-Knot Nematode) Contact Activity, Preventive,Drench Test

Cucumber cv. Toshka seeds were sown directly into pots filled with asandy substrate. Six days later pots were each treated with 5 ml of aWP10 suspension of the test compound at 20 ppm. Hereafter pots wereinoculated with 3000 eggs of M. incognita. The trial was harvestedfourteen days after trial application and inoculation. Root galling wasassessed according to Zeck's gall index (Zeck, 1971).

The following compounds showed a greater than 75% reduction of gallingcompared to the untreated control: A.1, A.2, A.3, A.6, A.7, A.12, A.14,A.15, A.17, A.19, A.21, A.22, A.23, A.24, A.25, A.27, A.28, A.31, A.32,A.35, A.36, A.37, A.38, A.49, A.50, A.56, A.57, A.58, A61 A.62, A.65,A.66, A.67, A.72, A.73, A.76, A.77, A.78, A.81, A.84, A.85, A.94, A.95,A.96, A.97, A.100, A.101.

The invention claimed is:
 1. A compound of the formula (I) wherein

wherein R1 is hydrogen, methyl or a halogen; R2 is hydrogen, methyl or ahalogen; R3 is hydrogen, methyl or a halogen; R4 is hydrogen, methyl ora halogen; R5 is substituted or unsubstituted phenyl group; R6 ishydrogen or C1-C4-alkyl; R7 is hydrogen, cyano, hydroxyl, formyl,C1-C4-alkyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl,C1-C4-alkoxy-C1-C4-alkyl, C1-C4-cyanoalkyl, C1-C4-alkylcarbonyl,C1-C4-alkoxycarbonyl, benzyl, C3-C6-cycloalkylcarbonyl orC3-C6-cycloalkoxycarbonyl; A1 is C—X, A2, A3 and A4 are C—H, and A5 isN; X is a halogen, OH, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxyor C1-C4-haloalkoxy.
 2. The compound according to claim 1 wherein R5 isa substituted phenyl having substituents independently selected fromhalogen, cyano, C1-C2-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy,C1-C4-haloalkoxy, C3-C6-cycloalkyl, which cycloalkyl is unsubstituted orsubstituted by one or more substituents Rx, where Rx is, independentlyof each other, is selected from halogen, C1-C4-alkyl, andC1-C4-haloalkyl.
 3. The compound according to claim 2 wherein thesubstituents on the phenyl at R5 are independently selected fromhalogen, cyano, C1-C4-haloalkyl, C1-C4-haloalkoxy, and C3-C6-cycloalkyl,which cycloalkyl is unsubstituted or substituted by one or moresubstituents Rx, where Rx is, independently of each other, is selectedfrom halogen, C1-C2-alkyl, and C1-C2 haloalkyl.
 4. A compositioncomprising a compound defined in claim 1 and an agronomic carrier andoptionally one or more customary formulation auxiliaries.
 5. Thecomposition according to claim 4 further comprising one or more otherbiologically active compounds.
 6. A treated plant propagation material,wherein adhered to the plant propagation material is an effective amountof a compound of formula (I) as defined in claim
 1. 7. The compoundaccording to claim 1 wherein A1 is C—X, A2, A3 and A4 are C—H, and A5 isN.
 8. The compound according to claim 1 wherein R5 is a substitutedphenyl having one to three substituents.
 9. The compound according toclaim 8 wherein the substituents are independently selected fromchlorine, methyl, fluorine, trifuoromethyl, cyclopropyl, and cyano. 10.The compound according to claim 1 wherein R6 is hydrogen or C1-C2-alkyl.11. The compound according to claim 1 wherein R7 is hydrogen.
 12. Thecompound according to claim 1 wherein X in CX of the A1 to A5 is,independently selected, from halogen, C1-C2-alkyl and C1-C2-haloalkyl.13. The compound according to claim 12 wherein X in CX of the A1 to A5is independently selected from chlorine, fluorine, methyl, andtrifluoromethyl.
 14. A method for protecting plant propagation materialfrom damage and/or yield loss caused by a pest and/or fungi whichcomprises applying to the propagation material or site, where thepropagation material is planted, an effective amount of a compound offormula (I) as defined in claim
 1. 15. A treated plant propagationmaterial, wherein adhered to the plant propagation material is aneffective amount of a compound of formula (I) as defined in claim
 1. 16.A pharmaceutical composition for the control of helminths, arachnids orarthropendo- or ectoparasites which comprises a compound of formula (I)as defined in claim 1, a physiologically tolerable carrier andoptionally one or more customary formulation auxiliaries.
 17. A methodfor the preparation of a composition for treating, controlling,preventing or protecting warm-blooded animals or fish againstinfestation or infection by helminths, arachnids or arthropendo- orectoparasites which comprises a compound of formula (I) as defined inclaim
 1. 18. A process for preparing a compound of formula (I)comprising reacting a compound of formula (II) and formula (VII)

wherein R1 to R7, A1, A2, A3, A4, and A5 are as defined in claim 1, andXb is a leaving group selected from halide and hydroxyl.